SherbyNet - /page/wikibook/entry.mu

Micron Document

<!DOCTYPE html>

<title>Wacker process</title>

</head>

Wacker process

</h1>

</header>

The Wacker process or the Hoechst-Wacker process (named after the chemical companies of the same name) is an industrial <a href="Chemical_reaction" title="Chemical reaction">chemical reaction</a>: the aerobic oxidation of <a href="Ethylene" title="Ethylene">ethylene</a> to <a href="Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> in the presence of <a href="Catalysis" title="Catalysis">catalytic</a>, aqueous <a href="Palladium(II)_chloride" title="Palladium(II) chloride">palladium(II) chloride</a> and <a href="Copper(II)_chloride" title="Copper(II) chloride">copper(II) chloride</a>.

The Tsuji-Wacker oxidation refers to a family of reactions inspired by the Wacker process. In Tsuji-Wacker reactions, palladium(II) catalyzes transformation of <a href="%CE%91-olefin" class="mw-redirect" title="Α-olefin">α-olefins</a> into <a href="Carbonyl_compounds" class="mw-redirect" title="Carbonyl compounds">carbonyl compounds</a> in various <a href="Solvent" title="Solvent">solvents</a>.

The development of the Wacker process popularized modern <a href="Organopalladium_chemistry" title="Organopalladium chemistry">organopalladium chemistry</a>, and Tsuji-Wacker oxidations remain in use today.

<div class="mw-heading mw-heading2"><h2 id="History">History</h2></div>

The Wacker process was one of the first <a href="Homogeneous_catalysis" title="Homogeneous catalysis">homogeneous catalysis</a> with <a href="Organopalladium" class="mw-redirect" title="Organopalladium">organopalladium</a> chemistry applied on an industrial scale.<a href="#cite_note-1">[1]</a>

In an 1893 doctoral dissertation on <a href="Marcellus_natural_gas_trend" title="Marcellus natural gas trend">Pennsylvanian natural gas</a>, Francis Clifford Phillips had reported that <a href="Palladium(II)_chloride" title="Palladium(II) chloride">palladium(II) chloride</a> oxidized ethylene to acetaldehyde, but the reaction required stoichiometric quantities of <a href="Palladium" title="Palladium">palladium</a>.<a href="#cite_note-2">[2]</a> It remained a niche curiosity until <a href="Wacker_Chemie" title="Wacker Chemie">Wacker Chemie</a> began developing its eponymous process in 1956.<a href="#cite_note-:2-3">[3]</a>

At the time, many industrial compounds were produced via acetaldehyde from <a href="Acetylene" title="Acetylene">acetylene</a>, itself from <a href="Calcium_carbide" title="Calcium carbide">calcium carbide</a>. The overall route exhibited poor thermodynamic efficiency and required great expense. Esso sought to market waste <a href="Olefin" class="mw-redirect" title="Olefin">olefins</a> from a new, under-construction <a href="Oil_refinery" title="Oil refinery">oil refinery</a> in <a href="Cologne" title="Cologne">Cologne</a> close to a Wacker site. Wacker realized that <a href="Ethylene" title="Ethylene">ethylene</a> would be a cheaper <a href="Feedstock" class="mw-redirect" title="Feedstock">feedstock</a> than acetylene, and began to investigate catalytic oxidation to <a href="Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a>.<a href="#cite_note-:2-3">[3]</a>

To Wacker's surprise, they smelled<a href="#cite_note-4">[Note 1]</a> not ethylene oxide but <a href="Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> in the product stream. From Phillips' dissertation, known properties of <a href="Zeise's_salt" title="Zeise's salt">Zeise's salt</a>, and transformation of the catalyst over the course of a batch reaction, Wacker realized that they needed to reoxidize the palladium to close the catalytic cycle.<a href="#cite_note-:2-3">[3]</a> They began publishing the process outline in 1957.<a href="#cite_note-5">[4]</a><a href="#cite_note-6">[5]</a> However, poor <a href="Patenting" class="mw-redirect" title="Patenting">patenting</a> strategy allowed <a href="Parent_corporation" class="mw-redirect" title="Parent corporation">parent</a> corporation <a href="Hoechst_AG" title="Hoechst AG">Hoechst AG</a> to outrace Wacker to the optimal catalysis conditions.<a href="#cite_note-:2-3">[3]</a><a href="#cite_note-7">[6]</a><a href="#cite_note-8">[7]</a>

Wacker-Hoechst began jointly constructing pilot plants in 1958, but the relatively aggressive reaction conditions required the first large-scale use of <a href="Titanium" title="Titanium">titanium</a> metal in the European chemical industry to protect against corrosion. Production plants started operation in 1960.<a href="#cite_note-:2-3">[3]</a>

The process also sparked a boom in <a href="Organopalladium_chemistry" title="Organopalladium chemistry">organopalladium chemistry</a>.<a href="#cite_note-:2-3">[3]</a> Studies from the 1960s elucidated several key points about the reaction mechanism through <a href="Kinetic_isotope_effect" title="Kinetic isotope effect">kinetic isotope effects</a> (or lack thereof) and <a href="Stereochemistry" title="Stereochemistry">stereochemistry</a>.<a href="#cite_note-:3-9">[8]</a><a href="#cite_note-K&H-10">[9]</a> Many focused on the hydroxypalladation step, which forms the C–O bond. Early reactions used conditions much milder than the industrial plants and obtained contradictory results; the modern consensus is that the step's stereochemistry is quite sensitive to chloride concentrations.<a href="#cite_note-K&H-10">[9]</a>

Other studies investigated reaction's application to more complex <a href="Terminal_alkene" title="Terminal alkene">terminal olefins</a>. High-order olefins are insoluble in water, but Clement and Selwitz<a href="#cite_note-11">[10]</a> found that aqueous <a href="Dimethylformamide" title="Dimethylformamide">DMF</a> as solvent allowed for the oxidation of 1-dodecene to 2-dodecanone. Fahey<a href="#cite_note-12">[11]</a> noted the use of 3-methylsulfolane in place of DMF as solvent increased the yield of oxidation of 3,3-Dimethylbut-1-ene. Two years after, Tsuji<a href="#cite_note-13">[12]</a> applied the Clement-Selwitz conditions for selective oxidations of terminal olefins with multiple functional groups, and demonstrated its utility in synthesis of complex substrates.<a href="#cite_note-14">[13]</a>

<a href="Carbonylation" title="Carbonylation">Carbonylation</a> has mainly superseded the Wacker process for modern <a href="Bulk_chemicals" class="mw-redirect" title="Bulk chemicals">bulk chemical</a> synthesis, but small-scale Tsuji-Wacker reactions remain important for <a href="Fine_chemical" title="Fine chemical">fine chemical</a> and laboratory-scale syntheses.<a href="#cite_note-:2-3">[3]</a>

<div class="mw-heading mw-heading2"><h2 id="Reaction_mechanism">Reaction mechanism</h2></div>

The <a href="Reaction_mechanism" title="Reaction mechanism">reaction mechanism</a> for the industrial Wacker process (olefin oxidation via palladium(II) chloride) has received significant attention for several decades. Aspects of the mechanism are still debated. A modern formulation is described below:<a href="#cite_note-15">[14]</a>

This reaction can also be described as follows:

followed by reactions that regenerate the Pd(II) catalyst:

/* start https://en.wikipedia.org/ */

.mw-parser-output .sfrac{white-space:nowrap}.mw-parser-output .sfrac.tion,.mw-parser-output .sfrac .tion{display:inline-block;vertical-align:-0.5em;font-size:85%;text-align:center}.mw-parser-output .sfrac .num{display:block;line-height:1em;margin:0.0em 0.1em;border-bottom:1px solid}.mw-parser-output .sfrac .den{display:block;line-height:1em;margin:0.1em 0.1em}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}

/* end https://en.wikipedia.org/ */

</style>⁠1/2⁠ O2 + 2 HCl → 2 CuCl2 + H2O</dd></dl>

Only the alkene and oxygen are consumed. Without <a href="Copper(II)_chloride" title="Copper(II) chloride">copper(II) chloride</a> as an <a href="Oxidizing_agent" title="Oxidizing agent">oxidizing agent</a>, Pd(0) metal (resulting from <a href="Beta-hydride_elimination" class="mw-redirect" title="Beta-hydride elimination">beta-hydride elimination</a> of Pd(II) in the final step) would precipitate, stopping Philips' reaction after one cycle. Air, pure oxygen, or a number of other reagents can then oxidise the resultant <a href="Copper(I)_chloride" title="Copper(I) chloride">CuCl</a>-chloride mixture back to CuCl2, allowing the cycle to continue.

High concentrations of chloride and <a href="Copper(II)_chloride" title="Copper(II) chloride">copper(II) chloride</a> favor formation of a new product, <a href="Ethylene_chlorohydrin" class="mw-redirect" title="Ethylene chlorohydrin">ethylene chlorohydrin</a>.<a href="#cite_note-16">[15]</a>

<div class="mw-heading mw-heading3"><h3 id="Evidence">Evidence</h3></div>

Evidence for the overall mechanism includes:<a href="#cite_note-:3-9">[8]</a><a href="#cite_note-K&H-10">[9]</a>

<ul><li>No H/D exchange effects. Experiments with C2D4 in water generate CD3CDO, and runs with C2H4 in D2O generate CH3CHO. Thus, <a href="Keto-enol_tautomerization" class="mw-redirect" title="Keto-enol tautomerization">keto-enol tautomerization</a> is not a possible mechanistic step.</li>

<li>Negligible <a href="Kinetic_isotope_effect" title="Kinetic isotope effect">kinetic isotope effect</a> with fully deuterated reactants (⁠k H/k D⁠=1.07). Hence hydride transfer is not <a href="Rate-determining_step" title="Rate-determining step">rate-determining</a>.</li>

<li>Significant competitive isotope effect with C2H2D2, (⁠k H/k D⁠= ~1.9), suggests that the rate determining step precedes acetaldehyde formation.</li></ul>

Evidence against the mechanism is a copper-chloride containing byproduct crystallized by Hosokawa et al.<a href="#cite_note-17">[16]</a> Questions remain about whether the cocatalyst also helps hydroxylate the ethylene ligand.

The ethylene ligand's hydroxylation is typically a slow process.<a href="#cite_note-:4-18">[17]</a><a href="#cite_note-:5-19">[18]</a> Depending on experimental conditions, it can occur either intramolecularly, from a palladium-bound hydroxido ligand, or intermolecularly. In the former case the hydroxylation is anti; in the latter, syn. Assuming small amounts of <a href="Copper" title="Copper">copper</a>, experiments have shown that syn addition occurs at low <a href="Chloride" title="Chloride">chloride</a> concentrations (< 1 <a href="Mole_(unit)" title="Mole (unit)">mol</a>/<a href="Liter" class="mw-redirect" title="Liter">L</a>, industrial process conditions)<a href="#cite_note-20">[19]</a> and anti addition occurs at high (> 3mol/L) concentrations.<a href="#cite_note-21">[20]</a><a href="#cite_note-22">[21]</a><a href="#cite_note-23">[22]</a><a href="#cite_note-24">[23]</a> The pathway change is probably due to chloride ions <a href="Catalyst_poisoning" title="Catalyst poisoning">saturating</a> the catalyst.<a href="#cite_note-:6-25">[24]</a><a href="#cite_note-:7-26">[25]</a> However, under strictly copper-free conditions, anti addition always occurs, and the rate no longer depends on the ethylene hydrogen isotopes.<a href="#cite_note-27">[26]</a><a href="#cite_note-28">[27]</a>

Another key step in the Wacker process is the migration of the hydrogen from oxygen to chloride, followed by <a href="Reductive_elimination" title="Reductive elimination">reductive elimination</a> to form the C-O double bond. This step is generally thought to proceed through a so-called <a href="%CE%92-hydride_elimination" class="mw-redirect" title="Β-hydride elimination">β-hydride elimination</a>:

The cyclic four-membered <a href="Transition_state" title="Transition state">transition state</a> shown above is unlikely. <a href="In_silico" title="In silico">In silico</a> studies<a href="#cite_note-29">[28]</a><a href="#cite_note-30">[29]</a><a href="#cite_note-31">[30]</a> argue that the <a href="Transition_state" title="Transition state">transition state</a> for this reaction step likely involves a 7-membered ring with a (solvent) water molecule acting as a catalyst.

<div class="mw-heading mw-heading2"><h2 id="Industrial_process">Industrial process</h2></div>

Two routes are commercialized for the production of acetaldehyde: one-stage process and two-stage. The acetaldehyde yield is about 95% in either, and byproducts are chlorinated hydrocarbons, chlorinated acetaldehydes, and acetic acid. In general, 100 parts of ethene gives:<a href="#cite_note-ullmann-32">[31]</a>

/* start https://en.wikipedia.org/ */

.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}

/* end https://en.wikipedia.org/ */

</style><div class="div-col">

<ul><li>95 parts acetaldehyde</li>

<li>1.9 parts chlorinated aldehydes</li>

<li>1.1 parts unconverted ethene</li>

<li>0.8 parts carbon dioxide</li>

<li>0.7 parts acetic acid</li>

<li>0.1 parts chloromethane</li>

<li>0.1 parts ethyl chloride</li>

<li>0.3 parts ethane, methane, crotonaldehyde</li></ul>

</div>

and other minor side products.

The production costs are virtually the same across the two processes; the advantage of using dilute gases in the two-stage method is balanced by higher investment costs. Due to the <a href="Corrosive" class="mw-redirect" title="Corrosive">corrosive</a> nature of the catalyst, either process requires a reactor lined with acid-proof <a href="Ceramic" title="Ceramic">ceramic</a> and <a href="Titanium" title="Titanium">titanium</a> tubing, but the two-stage process requires more reactors and piping. Generally, the choice of method is governed by the raw material and energy situations as well as by the availability of oxygen at a reasonable price.<a href="#cite_note-ullmann-32">[31]</a>

<div class="mw-heading mw-heading3"><h3 id="One-stage_process">One-stage process</h3></div>

<a href="Ethene" class="mw-redirect" title="Ethene">Ethene</a> and <a href="Oxygen" title="Oxygen">oxygen</a> are passed co-currently in a reaction tower at about 130 °C and 400 kPa.<a href="#cite_note-ullmann-32">[31]</a> The catalyst is an aqueous solution of <a href="Palladium_dichloride" class="mw-redirect" title="Palladium dichloride">PdCl2</a> and <a href="Copper_chloride" title="Copper chloride">CuCl2</a>. The acetaldehyde is purified by <a href="Extractive_distillation" title="Extractive distillation">extractive distillation</a> followed by <a href="Fractional_distillation" title="Fractional distillation">fractional distillation</a>. Extractive distillation with water removes the lights ends having lower boiling points than acetaldehyde (<a href="Chloromethane" title="Chloromethane">chloromethane</a>, <a href="Chloroethane" title="Chloroethane">chloroethane</a>, and <a href="Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>) at the top, while water and higher-boiling byproducts, such as <a href="Acetic_acid" title="Acetic acid">acetic acid</a>, <a href="Crotonaldehyde" title="Crotonaldehyde">crotonaldehyde</a> or chlorinated acetaldehydes, are withdrawn together with acetaldehyde at the bottom.<a href="#cite_note-ullmann-32">[31]</a>

<div class="mw-heading mw-heading3"><h3 id="Two-stage_process">Two-stage process</h3></div>

In two-stage process, reaction and <a href="Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> are carried out separately in tubular reactors. Unlike one-stage process, air can be used instead of oxygen. <a href="Ethylene" title="Ethylene">Ethylene</a> is passed through the reactor along with catalyst at 105–110 °C and 900–1000 kPa.<a href="#cite_note-ullmann-32">[31]</a> Catalyst solution containing acetaldehyde is separated by <a href="Flash_distillation" class="mw-redirect" title="Flash distillation">flash distillation</a>. The catalyst is oxidized in the oxidation reactor at 1000 kPa using air as oxidizing medium. Oxidized catalyst solution is separated and sent back to reactor. Oxygen from air is used up completely and the exhaust air is circulated as inert gas. Acetaldehyde – water vapor mixture is preconcentrated to 60–90% acetaldehyde by utilizing the <a href="Heat_of_reaction" class="mw-redirect" title="Heat of reaction">heat of reaction</a> and the discharged water is returned to the flash tower to maintain catalyst concentration. A two-stage distillation of the crude acetaldehyde follows. In the first stage, low-boiling substances, such as <a href="Chloromethane" title="Chloromethane">chloromethane</a>, <a href="Chloroethane" title="Chloroethane">chloroethane</a> and <a href="Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>, are separated. In the second stage, water and higher-boiling by-products, such as chlorinated acetaldehydes and <a href="Acetic_acid" title="Acetic acid">acetic acid</a>, are removed and acetaldehyde is obtained in pure form overhead.<a href="#cite_note-ullmann-32">[31]</a>

<div class="mw-heading mw-heading2"><h2 id="Tsuji-Wacker_oxidation">Tsuji-Wacker oxidation</h2></div>

Development of the reaction system has led to various catalytic systems to address selectivity of the reaction, as well as introduction of intermolecular and intramolecular oxidations with non-water nucleophiles.

<div class="mw-heading mw-heading3"><h3 id="Regioselectivity">Regioselectivity</h3></div>

<div class="mw-heading mw-heading4"><h4 id="Markovnikov_addition">Markovnikov addition</h4></div>

The oxidation of terminal olefins generally provide the <a href="Markovnikov's_rule" title="Markovnikov's rule">Markovnikov</a> ketone product. In rare cases where substrate favors the aldehyde (discussed below), different ligands can be used to enforce Markovnikov regioselectivity. <a href="Sparteine" title="Sparteine">Sparteine</a> (Figure 2, A)<a href="#cite_note-33">[32]</a> favors nucleopalladation at the terminal carbon to minimize steric interaction between the palladium complex and substrate. Quinox (Figure 2, B) favors ketone formation when the substrate contains a directing group.<a href="#cite_note-34">[33]</a> When such substrate bind to Pd(Quinox)(OOtBu), this complex is coordinately saturated which prevents the binding of the directing group, and results in formation of the Markovnikov product. The efficiency of this ligand is also attributed to its electronic property, where anionic TBHP prefers to bind <a href="Trans-alkene" class="mw-redirect" title="Trans-alkene">trans</a> to the oxazoline and olefin coordinate trans to the quinoline.<a href="#cite_note-35">[34]</a>

<div class="mw-heading mw-heading4"><h4 id="Anti-Markovnikov_addition">Anti-Markovnikov addition </h4></div>

The anti-Markovnikov addition selectivity to aldehyde can be achieved through exploiting inherent <a href="Stereoelectronics" class="mw-redirect" title="Stereoelectronics">stereoelectronics</a> of the substrate.<a href="#cite_note-Dong_734–744-36">[35]</a> Placement of directing group at homo-allylic (i.e. Figure 3, A)<a href="#cite_note-37">[36]</a> and <a href="Allyl" class="mw-redirect" title="Allyl">allylic</a> position (i.e. Figure 3, B)<a href="#cite_note-38">[37]</a> to the terminal olefin favors the anti-Markovnikov aldehyde product, which suggests that in the catalytic cycle the directing group <a href="Chelation" title="Chelation">chelates</a> to the palladium complex such that water attacks at the anti-Markovnikov carbon to generate the more thermodynamically stable palladacycle. Anti-Markovnikov selectivity is also observed in styrenyl substrates (i.e. Figure 3, C),<a href="#cite_note-39">[38]</a> presumably via η4-palladium-styrene complex after water attacks anti-Markovnikov. More examples of substrate-controlled, anti-Markovnikov Tsuji-Wacker Oxidation of olefins are given in reviews by Namboothiri,<a href="#cite_note-:0-40">[39]</a> Feringa,<a href="#cite_note-Dong_734–744-36">[35]</a> and Muzart.<a href="#cite_note-41">[40]</a>

Grubbs and co-workers paved way for anti-Markovnikov oxidation of <a href="Stereoelectronic" class="mw-redirect" title="Stereoelectronic">stereoelectronically</a> unbiased terminal olefins, through the use of palladium-nitrite system (Figure 2, D).<a href="#cite_note-42">[41]</a> In his system, the terminal olefin was oxidized to the aldehyde with high selectivity through a catalyst-control pathway. The mechanism is under investigation, however evidence<a href="#cite_note-:0-40">[39]</a> suggests it goes through a nitrite <a href="Radical_(chemistry)" title="Radical (chemistry)">radical</a> adds into the terminal carbon to generate the more thermodynamically stable, secondary radical. Grubbs expanded this methodology to more complex, unbiased olefins.<a href="#cite_note-43">[42]</a><a href="#cite_note-44">[43]</a>

<div class="mw-heading mw-heading3"><h3 id="Scope">Scope</h3></div>

<div class="mw-heading mw-heading4"><h4 id="Oxygen_nucleophiles">Oxygen nucleophiles </h4></div>

The intermolecular oxidations of olefins with alcohols as <a href="Nucleophile" title="Nucleophile">nucleophile</a> typically generate <a href="Ketal" class="mw-redirect" title="Ketal">ketals</a>, where as the palladium-catalyzed oxidations of olefins with carboxylic acids as nucleophile generates <a href="Vinylic" class="mw-redirect" title="Vinylic">vinylic</a> or allylic <a href="Carboxylate" title="Carboxylate">carboxylates</a>. In case of <a href="Diol" title="Diol">diols</a>, their reactions with alkenes typically generate ketals, whereas reactions of olefins bearing electron-withdrawing groups tend to form <a href="Acetal" title="Acetal">acetals</a>.<a href="#cite_note-:1-45">[44]</a>

Palladium-catalyzed intermolecular oxidations of <a href="Diene" title="Diene">dienes</a> with carboxylic acids and alcohols as donors give <a href="1%2C4-addition" class="mw-redirect" title="1,4-addition">1,4-addition</a> products. In the case of cyclohexadiene (Figure 4, A), Backvall found that <a href="Stereochemical" class="mw-redirect" title="Stereochemical">stereochemical</a> outcome of product was found to depend on concentration of LiCl.<a href="#cite_note-46">[45]</a> This reaction proceeds by first generating the Pd(OAc)(benzoquinone)(allyl) complex, through anti-nucleopalladation of diene with acetate as nucleophile. The absence of LiCl induces an <a href="Inner_sphere_electron_transfer" title="Inner sphere electron transfer">inner sphere</a> reductive elimination to afford the trans-acetate stereochemistry to give the trans-1,4-adduct. The presence of LiCl displaces acetate with chloride due to its higher binding affinity, which forces an outer sphere acetate attack anti to the palladium, and affords the cis-acetate stereochemistry to give the cis-1,4-adduct. Intramolecular oxidative cyclization: 2-(2-cyclohexenyl)phenol cyclizes to corresponding dihydro-benzofuran (Figure 4, B);<a href="#cite_note-47">[46]</a> 1-cyclohexadiene-acetic acid in presence of acetic acid cyclizes to corresponding lactone-acetate 1,4 adduct (Figure 4, C),<a href="#cite_note-48">[47]</a> with <a href="Cis-alkene" class="mw-redirect" title="Cis-alkene">cis</a> and <a href="Trans-alkene" class="mw-redirect" title="Trans-alkene">trans</a> selectivity controlled by LiCl presence.

<div class="mw-heading mw-heading4"><h4 id="Nitrogen_nucleophiles">Nitrogen nucleophiles</h4></div>

/* start https://en.wikipedia.org/ */

.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}

/* end https://en.wikipedia.org/ */

</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="Ammoxidation" title="Ammoxidation">Ammoxidation</a></div>

The oxidative <a href="Amination" title="Amination">aminations</a> of olefins are generally conducted with <a href="Amide" title="Amide">amides</a> or <a href="Imide" title="Imide">imides</a>; <a href="Amine" title="Amine">amines</a> are thought to be <a href="Protonation" title="Protonation">protonated</a> by the acidic medium or to bind the metal center too tightly to allow for the <a href="Catalysis" title="Catalysis">catalytic</a> chemistry to occur.<a href="#cite_note-:1-45">[44]</a> These nitrogen nucleophiles are found to be competent in both intermolecular and intramolecular reactions, some examples are depicted (Figure 5, A,<a href="#cite_note-49">[48]</a> B<a href="#cite_note-50">[49]</a>)

<div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2></div>

<li id="cite_note-4"><a href="#cite_ref-4">^</a> Wacker lacked a <a href="Gas_chromatography" title="Gas chromatography">gas chromatograph</a> at the time.<a href="#cite_note-:2-3">[3]</a>

</li>

</ol></div>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

/* start https://en.wikipedia.org/ */

.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}

/* end https://en.wikipedia.org/ */

</style><div class="reflist reflist-columns references-column-width reflist-columns-2">

<li id="cite_note-1"><a href="#cite_ref-1">^</a> Elschenbroich, C. "Organometallics" (2006) Wiley-VCH: Weinheim. <style data-mw-deduplicate="TemplateStyles:r1238218222">

/* start https://en.wikipedia.org/ */

.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("./mw/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("./mw/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("./mw/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("./mw/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}

/* end https://en.wikipedia.org/ */

</style><a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-3-527-29390-2</bdi>

</li>

<li id="cite_note-2"><a href="#cite_ref-2">^</a> <cite id="CITEREFPhillips1894" class="citation journal cs1">Phillips, Francis C. (March–June 1894). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IDogE3L1RLkC&pg=PA163">"Researches upon the phenomena of oxidation and chemical properties of gases"</a>. American Chemical Journal. 16 (3–6): 163–187, 255–277, 340–365, 406–429 – via Google Books. <q>The reaction between ethylene and palladium chloride in solution is of the second class and complete, the gas being rapidly absorbed. Palladium is deposited as a black powder, but no trace of oxidation to carbon dioxide occurs. The reaction is almost the same in the cold and at 100°. The gas escaping from the palladium-chloride solution (after complete reduction to metallic palladium) produces no precipitate in lime-water. The reaction between palladium chloride and ethylene leads to the production of aldehyde.</q></cite>

</li>

<li id="cite_note-:2-3">^ <a href="#cite_ref-:2_3-0">a</a> <a href="#cite_ref-:2_3-1">b</a> <a href="#cite_ref-:2_3-2">c</a> <a href="#cite_ref-:2_3-3">d</a> <a href="#cite_ref-:2_3-4">e</a> <a href="#cite_ref-:2_3-5">f</a> <a href="#cite_ref-:2_3-6">g</a> <a href="#cite_ref-:2_3-7">h</a> Acetaldehyde from Ethylene — A Retrospective on the Discovery of the Wacker Process Reinhard Jira <a href="Angew._Chem._Int._Ed." class="mw-redirect" title="Angew. Chem. Int. Ed.">Angew. Chem. Int. Ed.</a> 2009, 48, 9034–9037 <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.200903992">10.1002/anie.200903992</a>

</li>

<li id="cite_note-5"><a href="#cite_ref-5">^</a> J. Smidt, W. Hafner, R. Jira, J. Sedlmeier, R. Sieber, R. Rüttinger, and H. Kojer, Angew. Chem., 1959, 71, 176–182. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fange.19590710503">10.1002/ange.19590710503</a>

</li>

<li id="cite_note-6"><a href="#cite_ref-6">^</a> J. Smidt, W. Hafner, J. Sedlmeier, R. Jira, R. Rottinger (Cons. f.elektrochem.Ind.), DE 1 049 845, 1959, Anm. 04.01.1957.

</li>

<li id="cite_note-7"><a href="#cite_ref-7">^</a> W. Hafner, R. Jira, J. Sedlmeier, and J. Smidt, Chem. Ber., 1962, 95, 1575–1581. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.19620950702">10.1002/cber.19620950702</a>

</li>

<li id="cite_note-8"><a href="#cite_ref-8">^</a> J. Smidt, W. Hafner, R. Jira, R. Sieber, J. Sedlmeier, and A. Sabel, Angew. Chem. Int. Ed. Engl., 1962, 1, 80–88.

</li>

<li id="cite_note-:3-9">^ <a href="#cite_ref-:3_9-0">a</a> <a href="#cite_ref-:3_9-1">b</a> Henry, Patrick M. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley & Sons: New York, 2002; p 2119. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>0-471-31506-0</bdi>

</li>

<li id="cite_note-K&H-10">^ <a href="#cite_ref-K&H_10-0">a</a> <a href="#cite_ref-K&H_10-1">b</a> <a href="#cite_ref-K&H_10-2">c</a> <a href="#cite_ref-K&H_10-3">d</a> <cite id="CITEREFJ._A._KeithP._M._Henry2009" class="citation journal cs1">J. A. Keith; P. M. Henry (2009). "The Mechanism of the Wacker Reaction: A Tale of Two Hydroxypalladations". Angew. Chem. Int. Ed. 48 (48): 9038–9049. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.200902194">10.1002/anie.200902194</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19834921">19834921</a>.</cite>

</li>

<li id="cite_note-11"><a href="#cite_ref-11">^</a> <cite id="CITEREFClementSelwitz1964" class="citation journal cs1">Clement, William H.; Selwitz, Charles M. (January 1964). "Improved Procedures for Converting Higher α-Olefins to Methyl Ketones with Palladium Chloride". The Journal of Organic Chemistry. 29 (1): 241–243. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo01024a517">10.1021/jo01024a517</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite>

</li>

<li id="cite_note-12"><a href="#cite_ref-12">^</a> <cite id="CITEREFFaheyZeuch1974" class="citation journal cs1">Fahey, Darryl R.; Zeuch, Ernest A. (November 1974). "Aqueous sulfolane as solvent for rapid oxidation of higher .alpha.-olefins to ketones using palladium chloride". The Journal of Organic Chemistry. 39 (22): 3276–3277. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00936a023">10.1021/jo00936a023</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite>

</li>

<li id="cite_note-13"><a href="#cite_ref-13">^</a> <cite id="CITEREFTsujiShimizuYamamoto1976" class="citation journal cs1">Tsuji, Jiro; Shimizu, Isao; Yamamoto, Keiji (August 1976). "Convenient general synthetic method for 1,4- and 1,5-diketones by palladium catalyzed oxidation of α-allyl and α-3-butenyl ketones". Tetrahedron Letters. 17 (34): 2975–2976. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0040-4039%2801%2985504-0">10.1016/s0040-4039(01)85504-0</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0040-4039">0040-4039</a>.</cite>

</li>

<li id="cite_note-14"><a href="#cite_ref-14">^</a> <cite id="CITEREFTsuji1984" class="citation journal cs1">Tsuji, Jiro (1984). "Synthetic Applications of the Palladium-Catalyzed Oxidation of Olefins to Ketones". Synthesis. 1984 (5): 369–384. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-1984-30848">10.1055/s-1984-30848</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0039-7881">0039-7881</a>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:95604861">95604861</a>.</cite>

</li>

<li id="cite_note-15"><a href="#cite_ref-15">^</a> <cite id="CITEREFKurtiCzako2005" class="citation book cs1">Kurti, Laszlo; Czako, Barbara (2005). Strategic Applications of named Reactions in Organic Synthesis. 525 B Street, Suite 1900, San Diego, California 92101-4495, USA: Elsevier Academic Press. p. 474. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-12-429785-2</bdi>.</cite><code class="cs1-code">{{cite book}}</code>: CS1 maint: location (link)

</li>

<li id="cite_note-16"><a href="#cite_ref-16">^</a> H. Stangl and R. Jira, Tetrahedron Lett., 1970, 11, 3589–3592

</li>

<li id="cite_note-17"><a href="#cite_ref-17">^</a> T. Hosokawa, T. Nomura, S.-I. Murahashi, J. Organomet. Chem., 1998, 551, 387–389

</li>

<li id="cite_note-:4-18"><a href="#cite_ref-:4_18-0">^</a> Zaw, K., Lautens, M. and Henry P.M. Organometallics, 1985, 4, 1286–1296

</li>

<li id="cite_note-:5-19"><a href="#cite_ref-:5_19-0">^</a> Wan W.K., Zaw K., and Henry P.M. <a href="Organometallics" title="Organometallics">Organometallics</a>, 1988, 7, 1677–1683

</li>

<li id="cite_note-20"><a href="#cite_ref-20">^</a> P. M. Henry, J. Am. Chem. Soc., 1964, 86, 3246–3250.

</li>

<li id="cite_note-21"><a href="#cite_ref-21">^</a> James, D.E., Hines, L.F., Stille, J.K. J. Am. Chem. Soc., 1976, 98, 1806 <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00423a027">10.1021/ja00423a027</a>

</li>

<li id="cite_note-22"><a href="#cite_ref-22">^</a> James, D.E., Stille, J.K. J. Organomet. Chem., 1976, 108, 401. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00423a028">10.1021/ja00423a028</a>

</li>

<li id="cite_note-23"><a href="#cite_ref-23">^</a> Bäckvall, J.E., Akermark, B., Ljunggren, S.O., J. Am. Chem. Soc., 1979, 101, 2411. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00503a029">10.1021/ja00503a029</a>

</li>

<li id="cite_note-24"><a href="#cite_ref-24">^</a> Stille, J.K., Divakarumi, R.J., J. Organomet. Chem., 1979, 169, 239;

</li>

<li id="cite_note-:6-25"><a href="#cite_ref-:6_25-0">^</a> Francis, J.W., Henry, P.M. Organometallics, 1991, 10, 3498. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fom00056a019">10.1021/om00056a019</a>

</li>

<li id="cite_note-:7-26"><a href="#cite_ref-:7_26-0">^</a> Francis, J.W., Henry, P.M. Organometallics, 1992, 11, 2832.<a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fom00044a024">10.1021/om00044a024</a>

</li>

<li id="cite_note-27"><a href="#cite_ref-27">^</a> Comas-Vives, A., Stirling, A., Ujaque, G., Lledós, A., Chem. Eur. J., 2010, 16, 8738–8747.<a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fchem.200903522">10.1002/chem.200903522</a>

</li>

<li id="cite_note-28"><a href="#cite_ref-28">^</a> Anderson, B.J., Keith, J.A., and Sigman, M.S., J. Am. Chem. Soc., 2010, 132, 11872-11874

</li>

<li id="cite_note-29"><a href="#cite_ref-29">^</a> J. A. Keith, J. Oxgaard, and W. A. Goddard, III <a href="J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a>, 2006, 128, 3132 – 3133; <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja0533139">10.1021/ja0533139</a>

</li>

<li id="cite_note-30"><a href="#cite_ref-30">^</a> H. E. Hosseini, S. A. Beyramabadi, A. Morsali, and M. R. Housaindokht, J. Mol. Struct. (THEOCHEM), 2010, 941, 138–143

</li>

<li id="cite_note-31"><a href="#cite_ref-31">^</a> P. L. Theofanis, and W. A. Goddard, III Organometallics, 2011, 30, 4941 – 4948; <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fom200542w">10.1021/om200542w</a>

</li>

<li id="cite_note-ullmann-32">^ <a href="#cite_ref-ullmann_32-0">a</a> <a href="#cite_ref-ullmann_32-1">b</a> <a href="#cite_ref-ullmann_32-2">c</a> <a href="#cite_ref-ullmann_32-3">d</a> <a href="#cite_ref-ullmann_32-4">e</a> <a href="#cite_ref-ullmann_32-5">f</a> <cite id="CITEREFMarc_EckertGerald_FleischmannReinhard_JiraHermann_M._Bolt" class="citation encyclopaedia cs1">Marc Eckert; Gerald Fleischmann; Reinhard Jira; Hermann M. Bolt; Klaus Golka. "Acetaldehyde". <a href="Ullmann's_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a>. Weinheim: Wiley-VCH. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a01_031.pub2">10.1002/14356007.a01_031.pub2</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-3-527-30673-2</bdi>.</cite>

</li>

<li id="cite_note-33"><a href="#cite_ref-33">^</a> <cite id="CITEREFBalijaStowersSchultzSigman2006" class="citation journal cs1">Balija, Amy M.; Stowers, Kara J.; Schultz, Mitchell J.; Sigman, Matthew S. (March 2006). "Pd(II)-Catalyzed Conversion of Styrene Derivatives to Acetals: Impact of (−)-Sparteine on Regioselectivity". Organic Letters. 8 (6): 1121–1124. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fol053110p">10.1021/ol053110p</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1523-7060">1523-7060</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16524283">16524283</a>.</cite>

</li>

<li id="cite_note-34"><a href="#cite_ref-34">^</a> <cite id="CITEREFMichelCamelioCornellSigman2009" class="citation journal cs1">Michel, Brian W.; Camelio, Andrew M.; Cornell, Candace N.; Sigman, Matthew S. (2009-05-06). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2763354">"A General and Efficient Catalyst System for a Wacker-Type Oxidation Using TBHP as the Terminal Oxidant: Application to Classically Challenging Substrates"</a>. Journal of the American Chemical Society. 131 (17): 6076–6077. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2009JAChS.131.6076M">2009JAChS.131.6076M</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja901212h">10.1021/ja901212h</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2763354">2763354</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19364100">19364100</a>.</cite>

</li>

<li id="cite_note-35"><a href="#cite_ref-35">^</a> <cite id="CITEREFMichelSteffensSigman2011" class="citation journal cs1">Michel, Brian W.; Steffens, Laura D.; Sigman, Matthew S. (June 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3113657">"On the Mechanism of the Palladium-Catalyzed tert -Butylhydroperoxide-Mediated Wacker-Type Oxidation of Alkenes Using Quinoline-2-Oxazoline Ligands"</a>. Journal of the American Chemical Society. 133 (21): 8317–8325. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2011JAChS.133.8317M">2011JAChS.133.8317M</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja2017043">10.1021/ja2017043</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3113657">3113657</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21553838">21553838</a>.</cite>

</li>

<li id="cite_note-Dong_734–744-36">^ <a href="#cite_ref-Dong_734–744_36-0">a</a> <a href="#cite_ref-Dong_734–744_36-1">b</a> <cite id="CITEREFDongBrowneFeringa2014" class="citation journal cs1">Dong, Jia Jia; Browne, Wesley R.; Feringa, Ben L. (2014-11-03). <a rel="nofollow" class="external text" href="https://pure.rug.nl/ws/files/240464098/Angew_Chem_Int_Ed_2014_Dong_Palladium_Catalyzed_anti_Markovnikov_Oxidation_of_Terminal_Alkenes.pdf">"Palladium-Catalyzed anti-Markovnikov Oxidation of Terminal Alkenes"</a> (PDF). Angewandte Chemie International Edition. 54 (3): 734–744. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201404856">10.1002/anie.201404856</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1433-7851">1433-7851</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25367376">25367376</a>.</cite>

</li>

<li id="cite_note-37"><a href="#cite_ref-37">^</a> <cite id="CITEREFMillerWayner1990" class="citation journal cs1">Miller, D. G.; Wayner, Danial D. M. (April 1990). "Improved method for the Wacker oxidation of cyclic and internal olefins". The Journal of Organic Chemistry. 55 (9): 2924–2927. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00296a067">10.1021/jo00296a067</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite>

</li>

<li id="cite_note-38"><a href="#cite_ref-38">^</a> <cite id="CITEREFStragiesBlechert2000" class="citation journal cs1">Stragies, Roland; Blechert, Siegfried (October 2000). "Enantioselective Synthesis of Tetraponerines by Pd- and Ru-Catalyzed Domino Reactions". Journal of the American Chemical Society. 122 (40): 9584–9591. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2000JAChS.122.9584S">2000JAChS.122.9584S</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja001688i">10.1021/ja001688i</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>.</cite>

</li>

<li id="cite_note-39"><a href="#cite_ref-39">^</a> <cite id="CITEREFWrightGauntSpencer2006" class="citation journal cs1">Wright, Joseph A.; Gaunt, Matthew J.; Spencer, Jonathan B. (2006-01-11). "Novel Anti-Markovnikov Regioselectivity in the Wacker Reaction of Styrenes". Chemistry - A European Journal. 12 (3): 949–955. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fchem.200400644">10.1002/chem.200400644</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0947-6539">0947-6539</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16144020">16144020</a>.</cite>

</li>

<li id="cite_note-:0-40">^ <a href="#cite_ref-:0_40-0">a</a> <a href="#cite_ref-:0_40-1">b</a> <cite id="CITEREFBaijuGravelDorisNamboothiri2016" class="citation journal cs1">Baiju, Thekke Veettil; Gravel, Edmond; Doris, Eric; Namboothiri, Irishi N.N. (September 2016). "Recent developments in Tsuji-Wacker oxidation". Tetrahedron Letters. 57 (36): 3993–4000. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tetlet.2016.07.081">10.1016/j.tetlet.2016.07.081</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0040-4039">0040-4039</a>.</cite>

</li>

<li id="cite_note-41"><a href="#cite_ref-41">^</a> <cite id="CITEREFMuzart2007" class="citation journal cs1">Muzart, Jacques (August 2007). "Aldehydes from Pd-catalysed oxidation of terminal olefins". Tetrahedron. 63 (32): 7505–7521. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tet.2007.04.001">10.1016/j.tet.2007.04.001</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0040-4020">0040-4020</a>.</cite>

</li>

<li id="cite_note-42"><a href="#cite_ref-42">^</a> <cite id="CITEREFWickensMorandiGrubbs2013" class="citation journal cs1">Wickens, Zachary K.; Morandi, Bill; Grubbs, Robert H. (2013-09-13). <a rel="nofollow" class="external text" href="https://authors.library.caltech.edu/42230/7/anie_201306756_sm_miscellaneous_information.pdf">"Aldehyde-Selective Wacker-Type Oxidation of Unbiased Alkenes Enabled by a Nitrite Co-Catalyst"</a> (PDF). Angewandte Chemie International Edition. 52 (43): 11257–11260. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201306756">10.1002/anie.201306756</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1433-7851">1433-7851</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24039135">24039135</a>.</cite>

</li>

<li id="cite_note-43"><a href="#cite_ref-43">^</a> <cite id="CITEREFWickensSkakujMorandiGrubbs2014" class="citation journal cs1">Wickens, Zachary K.; Skakuj, Kacper; Morandi, Bill; Grubbs, Robert H. (2014-01-13). <a rel="nofollow" class="external text" href="https://authors.library.caltech.edu/43469/7/ja411749k_si_001.pdf">"Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes"</a> (PDF). Journal of the American Chemical Society. 136 (3): 890–893. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2014JAChS.136..890W">2014JAChS.136..890W</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja411749k">10.1021/ja411749k</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24410719">24410719</a>.</cite>

</li>

<li id="cite_note-44"><a href="#cite_ref-44">^</a> <cite id="CITEREFKimLiGrubbsStoltz2016" class="citation journal cs1">Kim, Kelly E.; Li, Jiaming; Grubbs, Robert H.; Stoltz, Brian M. (2016-09-30). <a rel="nofollow" class="external text" href="https://authors.library.caltech.edu/70776/2/ja6b08788_si_001.pdf">"Catalytic Anti-Markovnikov Transformations of Hindered Terminal Alkenes Enabled by Aldehyde-Selective Wacker-Type Oxidation"</a> (PDF). Journal of the American Chemical Society. 138 (40): 13179–13182. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2016JAChS.13813179K">2016JAChS.13813179K</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjacs.6b08788">10.1021/jacs.6b08788</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27670712">27670712</a>.</cite>

</li>

<li id="cite_note-:1-45">^ <a href="#cite_ref-:1_45-0">a</a> <a href="#cite_ref-:1_45-1">b</a> <cite id="CITEREFHartwig2010" class="citation book cs1">Hartwig, John F. (2010). Organotransition Metal Chemistry: From Bonding to Catalysis. USA: University Science Books. pp. 717–734. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-1-891389-53-5</bdi>.</cite>

</li>

<li id="cite_note-46"><a href="#cite_ref-46">^</a> <cite id="CITEREFBaeckvallBystroemNordberg1984" class="citation journal cs1">Baeckvall, Jan E.; Bystroem, Styrbjoern E.; Nordberg, Ruth E. (November 1984). "Stereo- and regioselective palladium-catalyzed 1,4-diacetoxylation of 1,3-dienes". The Journal of Organic Chemistry. 49 (24): 4619–4631. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00198a010">10.1021/jo00198a010</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite>

</li>

<li id="cite_note-47"><a href="#cite_ref-47">^</a> <cite id="CITEREFHosokawaMiyagiMurahashiSonoda1978" class="citation journal cs1">Hosokawa, Takahiro; Miyagi, Shyogo; Murahashi, Shunichi; Sonoda, Akio (July 1978). "Oxidative cyclization of 2-allylphenols by palladium(II) acetate. Changes in product distribution". The Journal of Organic Chemistry. 43 (14): 2752–2757. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00408a004">10.1021/jo00408a004</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite>

</li>

<li id="cite_note-48"><a href="#cite_ref-48">^</a> <cite id="CITEREFBaeckvallGranbergAnderssonGatti1993" class="citation journal cs1">Baeckvall, Jan E.; Granberg, Kenneth L.; Andersson, Pher G.; Gatti, Roberto; Gogoll, Adolf (September 1993). "Stereocontrolled lactonization reactions via palladium-catalyzed 1,4-addition to conjugated dienes". The Journal of Organic Chemistry. 58 (20): 5445–5451. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00072a029">10.1021/jo00072a029</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite>

</li>

<li id="cite_note-49"><a href="#cite_ref-49">^</a> <cite id="CITEREFTimokhinStahl2005" class="citation journal cs1">Timokhin, Vitaliy I.; Stahl, Shannon S. (December 2005). "Brønsted Base-Modulated Regioselectivity in the Aerobic Oxidative Amination of Styrene Catalyzed by Palladium". Journal of the American Chemical Society. 127 (50): 17888–17893. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2005JAChS.12717888T">2005JAChS.12717888T</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja0562806">10.1021/ja0562806</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16351120">16351120</a>.</cite>

</li>

<li id="cite_note-50"><a href="#cite_ref-50">^</a> <cite id="CITEREFLarockHightowerHasvoldPeterson1996" class="citation journal cs1">Larock, Richard C.; Hightower, Timothy R.; Hasvold, Lisa A.; Peterson, Karl P. (January 1996). "Palladium(II)-Catalyzed Cyclization of Olefinic Tosylamides". The Journal of Organic Chemistry. 61 (11): 3584–3585. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo952088i">10.1021/jo952088i</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11667199">11667199</a>.</cite>

</li>

</ol></div>

/* start https://en.wikipedia.org/ */

.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}

/* end https://en.wikipedia.org/ */

</style><style data-mw-deduplicate="TemplateStyles:r1236075235">

/* start https://en.wikipedia.org/ */

.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}

/* end https://en.wikipedia.org/ */

</style><style data-mw-deduplicate="TemplateStyles:r1123817410">

/* start https://en.wikipedia.org/ */

.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}

/* end https://en.wikipedia.org/ */

</style></div><div role="navigation" class="navbox" aria-labelledby="Alkenes39" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><style data-mw-deduplicate="TemplateStyles:r1239400231">

/* start https://en.wikipedia.org/ */

.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}

/* end https://en.wikipedia.org/ */

</style><div id="Alkenes39" style="font-size:114%;margin:0 4em"><a href="Alkene" title="Alkene">Alkenes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Ethylene" title="Ethylene">Ethene</a> (C2H4)</li>

<li><a href="Propene" class="mw-redirect" title="Propene">Propene</a> (C3H6)</li>

<li><a href="Butene" title="Butene">Butene</a> (C4H8)</li>

<li><a href="Pentene" title="Pentene">Pentene</a> (C5H10)</li>

<li><a href="Hexene" title="Hexene">Hexene</a> (C6H12)</li>

<li><a href="Heptene" title="Heptene">Heptene</a> (C7H14)</li>

<li><a href="Octene" title="Octene">Octene</a> (C8H16)</li>

<li><a href="Nonene" title="Nonene">Nonene</a> (C9H18)</li>

<li><a href="Decene" title="Decene">Decene</a> (C10H20)</li>

<li><a href="Polyene" title="Polyene">Polyenes</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Preparations</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Dehydrohalogenation" title="Dehydrohalogenation">Dehydrohalogenation</a> from <a href="Haloalkane" title="Haloalkane">haloalkane</a></li>

<li><a href="Dehydration_reaction" title="Dehydration reaction">Dehydration reaction</a> from <a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a></li>

<li><a href="Semihydrogenation" class="mw-redirect" title="Semihydrogenation">Semihydrogenation</a> from <a href="Alkyne" title="Alkyne">alkyne</a></li>

<li><a href="Bamford%E2%80%93Stevens_reaction" title="Bamford–Stevens reaction">Bamford–Stevens reaction</a></li>

<li><a href="Barton%E2%80%93Kellogg_reaction" title="Barton–Kellogg reaction">Barton–Kellogg reaction</a></li>

<li><a href="Boord_olefin_synthesis" title="Boord olefin synthesis">Boord olefin synthesis</a></li>

<li><a href="Chugaev_elimination" title="Chugaev elimination">Chugaev elimination</a></li>

<li><a href="Cope_reaction" title="Cope reaction">Cope reaction</a></li>

<li><a href="Corey%E2%80%93Winter_olefin_synthesis" title="Corey–Winter olefin synthesis">Corey–Winter olefin synthesis</a></li>

<li><a href="Grieco_elimination" title="Grieco elimination">Grieco elimination</a></li>

<li><a href="Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a></li>

<li><a href="Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a></li>

<li><a href="Hydrazone_iodination" title="Hydrazone iodination">Hydrazone iodination</a></li>

<li><a href="Julia_olefination" title="Julia olefination">Julia olefination</a></li>

<li><a href="Kauffmann_olefination" title="Kauffmann olefination">Kauffmann olefination</a></li>

<li><a href="McMurry_reaction" title="McMurry reaction">McMurry reaction</a></li>

<li><a href="Peterson_olefination" title="Peterson olefination">Peterson olefination</a></li>

<li><a href="Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li>

<li><a href="Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li>

<li><a href="Takai_olefination" title="Takai olefination">Takai olefination</a></li>

<li><a href="Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li>

<li><a href="Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a></li>

<li><a href="Ene_reaction" title="Ene reaction">Ene reaction</a></li>

<li><a href="Cope_rearrangement" title="Cope rearrangement">Cope rearrangement</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Hydrogenation" title="Hydrogenation">Hydrogenation</a></li>

<li><a href="Halogenation" title="Halogenation">Halogenation</a></li>

<li><a href="Hydration_reaction" title="Hydration reaction">Hydration</a></li>

<li><a href="Electrophilic_addition" title="Electrophilic addition">Electrophilic addition</a></li>

<li><a href="Oxymercuration_reaction" title="Oxymercuration reaction">Oxymercuration reaction</a></li>

<li><a href="Hydroboration" title="Hydroboration">Hydroboration</a></li>

<li><a href="Cyclopropanation" title="Cyclopropanation">Cyclopropanation</a></li>

<li><a href="Epoxidation" class="mw-redirect" title="Epoxidation">Epoxidation</a></li>

<li><a href="Dihydroxylation" title="Dihydroxylation">Dihydroxylation</a></li>

<li><a href="Ozonolysis" title="Ozonolysis">Ozonolysis</a></li>

<li><a href="Hydrohalogenation" title="Hydrohalogenation">Hydrohalogenation</a></li>

<li><a href="Polymerization" title="Polymerization">Polymerization</a></li>

<li><a href="Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li>

<li><a href="Dehydrogenation" title="Dehydrogenation">Dehydrogenation</a></li>

<li><a href="Ene_reaction" title="Ene reaction">Ene reaction</a></li>

<li><a href="Friedel-Crafts_Alkylation" class="mw-redirect" title="Friedel-Crafts Alkylation">Friedel-Crafts Alkylation</a></li></ul>

</div></td></tr></tbody></table></div>

<div class="navbox-styles"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox390" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Authority control databases: National </th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4313257-1">Germany</a></li></ul></div></td></tr></tbody></table></div></div><div><div class="zim-footer">

This article is issued from <a class="external text" title="Last edited on 2025-07-03" href="https://en.wikipedia.org/wiki/?title=Wacker_process&oldid=1298614372">Wikipedia</a>. The text is available under <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">Creative Commons Attribution-Share Alike 4.0</a> unless otherwise noted. Additional terms may apply for the media files.

</div>

</div></div>

</div>

</main>

</div>

</body></html>