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<title>Dess–Martin periodinane</title>

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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Dess–Martin periodinane</span></span>

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<caption>Dess–Martin periodinane

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names

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<td colspan="2" style="text-align:left;"><a href="Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a>

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">3-Oxo-1λ<sup>5</sup>,2-benziodoxole-1,1,1(3<i>H</i>)-triyl triacetate</div></div>

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<td colspan="2" style="text-align:left;">Other names

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Dess–Martin periodinane</div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div>

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</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=87413-09-0">87413-09-0</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div>

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<td><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29OI1%28c2ccccc2C%28%3DO%29O1%29%28OC%28%3DO%29C%29OC%28%3DO%29C">Interactive image</a></span></li></ul></div>

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<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>

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<td><a href="ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div>

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<td><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID30236335">DTXSID30236335</a> </span></li></ul></div>

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<div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div>

<ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H13IO8/c1-8(15)19-14(20-9(2)16,21-10(3)17)12-7-5-4-6-11(12)13(18)22-14/h4-7H,1-3H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: NKLCNNUWBJBICK-UHFFFAOYSA-N</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H13IO8/c1-8(15)19-14(20-9(2)16,21-10(3)17)12-7-5-4-6-11(12)13(18)22-14/h4-7H,1-3H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: NKLCNNUWBJBICK-UHFFFAOYAQ</div></div></li></ul>

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<div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Chemical_formula" title="Chemical formula">Chemical formula</a></div>

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<td><a href="Molar_mass" title="Molar mass">Molar mass</a>

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<td>424.14 g/mol

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<td>Appearance

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<td>white powder, chips,<br>crystals or crystalline<br>powder and/or chunks

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<td><a href="Density" title="Density">Density</a>

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<td>1.362 g/cm<sup>3</sup> solid

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<td><a href="Melting_point" title="Melting point">Melting point</a>

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<td>103 to 133 °C (217 to 271 °F; 376 to 406 K)

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div>

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<td><a href="2-Iodoxybenzoic_acid" title="2-Iodoxybenzoic acid">2-Iodoxybenzoic acid</a>

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<td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div>

<div style="margin-top: 0.3em; text-align: center;">Infobox references</div>

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<p><b>Dess–Martin periodinane</b> (<b>DMP</b>) is a <a href="Chemical_reagent" class="mw-redirect" title="Chemical reagent">chemical reagent</a> used in the <a href="Dess%E2%80%93Martin_oxidation" title="Dess–Martin oxidation">Dess–Martin oxidation</a>, <a href="Alcohol_oxidation" title="Alcohol oxidation">oxidizing primary alcohols</a> to <a href="Aldehyde" title="Aldehyde">aldehydes</a> and secondary <a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> to <a href="Ketone" title="Ketone">ketones</a>.<sup id="cite_ref-Dess_Martin_1983_1-0" class="reference"><a href="#cite_note-Dess_Martin_1983-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> This <a href="Periodinane" title="Periodinane">periodinane</a> has several advantages over <a href="Chromium" title="Chromium">chromium</a>- and <a href="Dimethyl_sulfoxide" title="Dimethyl sulfoxide">DMSO</a>-based oxidants that include milder conditions (room temperature, neutral pH), shorter reaction times, higher yields, simplified workups, high chemoselectivity, tolerance of sensitive functional groups, and a long shelf life. However, use on an industrial scale is made difficult by its cost and its potentially explosive nature.<sup id="cite_ref-Plumb_3-0" class="reference"><a href="#cite_note-Plumb-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is named after the American chemists Daniel Benjamin Dess and <a href="James_Cullen_Martin" title="James Cullen Martin">James Cullen Martin</a> who developed the reagent in 1983. It is based on <a href="2-Iodoxybenzoic_acid" title="2-Iodoxybenzoic acid">IBX</a>, but due to the acetate groups attached to the central iodine atom, DMP is much more reactive than IBX and is much more soluble in organic solvents.<sup id="cite_ref-Dess_Martin_1991_4-0" class="reference"><a href="#cite_note-Dess_Martin_1991-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

</p>

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

<p>The most friendly synthesis of IBX has been determined to be treating <a href="2-Iodobenzoic_acid" title="2-Iodobenzoic acid">2-iodobenzoic acid</a> with <a href="Oxone" class="mw-redirect" title="Oxone">oxone</a> in water, at elevated temperatures for 3 hours.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> IBX is then acylated using Ireland and Liu’s

<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> modifications from the original procedure. These modifications allowed for higher yields and a simplified work up procedure. The resulted solids can be obtained via filtration and washing with ether. Ireland and Liu used a catalytic amount of <a href="Tosylic_acid" class="mw-redirect" title="Tosylic acid">tosylic acid</a>, which allowed the reaction to complete in less than 2 hours (compared to the classic synthesis, utilizing 24 hours) and in yields exceeding 90%.

</p>

<p>The classic method presented by R. K. Boeckman and J. J. Mullins<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> involved heating a solution of <a href="Potassium_bromate" title="Potassium bromate">potassium bromate</a>, <a href="Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>, <a href="2-iodobenzoic_acid" class="mw-redirect" title="2-iodobenzoic acid">2-iodobenzoic acid</a> to afford IBX (1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide, <a href="2-Iodoxybenzoic_acid" title="2-Iodoxybenzoic acid">2-iodoxybenzoic acid</a>). IBX was then acylated using acetic acid and <a href="Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a>.

</p>

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

<p>DMP has <a href="Square_pyramidal_molecular_geometry" title="Square pyramidal molecular geometry">square pyramidal</a> geometry with 4 heteroatoms in basal positions and one apical phenyl group.

</p>

<div class="mw-heading mw-heading2"><h2 id="Oxidation_mechanism">Oxidation mechanism</h2></div>

<p>Dess–Martin periodinane is mainly used as an <a href="Oxidant" class="mw-redirect" title="Oxidant">oxidant</a> for complex, sensitive and multifunctional <a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>. One of the reasons for its effectiveness is its high selectivity towards complexation of the <a href="Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group, which allows alcohols to rapidly perform <a href="Ligand" title="Ligand">ligand</a> exchange; the first step in the oxidation reaction.

</p><p><a href="Proton_NMR" class="mw-redirect" title="Proton NMR">Proton NMR</a> has indicated that using one equivalent of alcohol forms the intermediate diacetoxyalkoxyperiodinane. The acetate then acts as a base to deprotonate the α-H from the alcohol to afford the <a href="Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> compound, iodinane, and <a href="Acetic_acid" title="Acetic acid">acetic acid</a>.

</p><p>When a <a href="Diol" title="Diol">diol</a> or more than one equivalent of alcohol is used, acetoxydialkoxyperiodinane is formed instead. Due to the <a href="Labile" class="mw-redirect" title="Labile">labile</a> nature of this particular periodinane, oxidation occurs much faster.<sup id="cite_ref-Dess_Martin_1991_4-1" class="reference"><a href="#cite_note-Dess_Martin_1991-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

</p>

<p>Schreiber and coworkers have shown that water increases the rate of the oxidation reaction.<sup id="cite_ref-Meyers_Water_1994_8-0" class="reference"><a href="#cite_note-Meyers_Water_1994-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Dess and Martin had originally observed that the oxidation of ethanol was increased when there was an extra equivalent of ethanol. It is believed that the rate of dissociation of the final acetate ligand from the iodine is increased, because of the <a href="Electron_donor" title="Electron donor">electron-donating</a> ability of the hydroxyl group (thus weakening the I-OAc bond).<sup id="cite_ref-Dess_Martin_1991_4-2" class="reference"><a href="#cite_note-Dess_Martin_1991-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

</p>

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

<p>Using the standard Dess–Martin periodinane conditions, alcohols can be oxidized to aldehydes/ketones without affecting <a href="Furan" title="Furan">furan</a> rings, <a href="Sulfides" class="mw-redirect" title="Sulfides">sulfides</a>, <a href="Enol_ether" title="Enol ether">vinyl ethers</a>, and secondary <a href="Amides" class="mw-redirect" title="Amides">amides</a>.<sup id="cite_ref-Dess_Martin_1991_4-3" class="reference"><a href="#cite_note-Dess_Martin_1991-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Allylic alcohols are easily oxidized using DMP, which are typically difficult to convert to their respective carbonyls using the typical oxidants.<sup id="cite_ref-Lawrence_2001_9-0" class="reference"><a href="#cite_note-Lawrence_2001-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>

</p><p>Myers and coworkers determined that DMP could oxidize N-protected-amino alcohols, without epimerization (unlike most other oxidants, including Swern oxidation). These protected amino alcohols can be very important in the pharmaceutical industry.<sup id="cite_ref-Myers_2000_10-0" class="reference"><a href="#cite_note-Myers_2000-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>

</p><p>Benzylic and allylic alcohols react faster than saturated alcohols,<sup id="cite_ref-Dess_Martin_1991_4-4" class="reference"><a href="#cite_note-Dess_Martin_1991-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> while DMP oxidizes aldoximes and ketoximes to their respective aldehydes and ketones, faster than a primary, secondary or benzylic alcohol to its respective carbonyl.<sup id="cite_ref-Chaudhari_11-0" class="reference"><a href="#cite_note-Chaudhari-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup>

</p><p>One example of the Dess–Martin oxidation involves transforming a sensitive α-β-unsaturated alcohol to its corresponding aldehyde. This moiety has been found in several natural products and due to its high functionality, it could be a valuable synthetic building block in organic synthesis. Thongsornkleeb and Danheiser oxidized this sensitive alcohol by employing the Dess Martin Oxidation and altering the work up procedure (diluting with pentanes, washing with poly(<a href="4-Vinylpyridine" title="4-Vinylpyridine">4-vinylpyridine</a>) to remove the acetic acid generated during the reaction, filtering and concentrating via distillation.<sup id="cite_ref-application_12-0" class="reference"><a href="#cite_note-application-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading3"><h3 id="t-Butyl_DMP"><i>t</i>-Butyl DMP</h3></div>

<p>Difluoro and monofluoro alcohols are more difficult to oxidize. <a href="Swern_oxidation" title="Swern oxidation">Swern oxidation</a> has been used, but a large excess of the oxidant had to be employed, and in some cases did not give reproducible results. Linderman and Graves<sup id="cite_ref-Linderman_1989_13-0" class="reference"><a href="#cite_note-Linderman_1989-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> found DMP was successful in most cases but could not tolerate the presence of <a href="Nucleophile" title="Nucleophile">nucleophilic</a> functional groups in the alcohol, as these reacted with DMP by displacing acetate. Using the compound shown below produced the desired carbonyls in high yields as the addition of the <a href="Butoxy" class="mw-redirect" title="Butoxy"><i>tert</i>-butoxy</a> group, due to its <a href="Steric_effects" title="Steric effects">steric bulk</a>, minimizes these side reactions.

</p>

<ul><li><a href="Alcohol_oxidation" title="Alcohol oxidation">Alcohol oxidation</a></li>

<li><a href="Pyridinium_chlorochromate" title="Pyridinium chlorochromate">Pyridinium chlorochromate</a></li>

<li><a href="Jones_oxidation" title="Jones oxidation">Jones oxidation</a></li>

<li><a href="Oppenauer_oxidation" title="Oppenauer oxidation">Oppenauer oxidation</a></li>

<li><a href="Pfitzner%E2%80%93Moffatt_oxidation" title="Pfitzner–Moffatt oxidation">Pfitzner–Moffatt oxidation</a></li>

<li><a href="Parikh%E2%80%93Doering_oxidation" title="Parikh–Doering oxidation">Parikh–Doering oxidation</a></li>

<li><a href="Albright-Goldman_oxidation" class="mw-redirect" title="Albright-Goldman oxidation">Albright-Goldman oxidation</a></li>

<li><a href="Swern_oxidation" title="Swern oxidation">Swern oxidation</a></li>

<li><a href="Corey%E2%80%93Kim_oxidation" title="Corey–Kim oxidation">Corey–Kim oxidation</a></li>

<li><a href="Ley_oxidation" class="mw-redirect" title="Ley oxidation">Ley oxidation</a> (<a href="Tetrapropylammonium_perruthenate" title="Tetrapropylammonium perruthenate">TPAP</a> oxidation)</li>

<li><a href="TEMPO" title="TEMPO">TEMPO</a> oxidation</li></ul>

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

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</style><cite id="CITEREFDess,_D._B.Martin,_J._C.1983" class="citation journal cs1">Dess, D. B.; Martin, J. C. (1983). "Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones". <i><a href="J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a></i> <b>48</b> (22): <span class="nowrap">4155–</span>4156. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00170a070">10.1021/jo00170a070</a>.</cite></span>

</li>

<li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><cite id="CITEREFBoeckmanGeorge2009" class="citation book cs1">Boeckman, Robert J.; George, Kelly M. (2009). "1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one". <i>Encyclopedia of Reagents for Organic Synthesis</i>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F047084289X.rt157m.pub2">10.1002/047084289X.rt157m.pub2</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0471936237</bdi>.</cite></span>

</li>

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<li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><cite id="CITEREFIreland,_R._E.Liu,_L.1993" class="citation journal cs1">Ireland, R. E.; Liu, L. (1993). "An improved procedure for the preparation of the Dess-Martin periodinane". <i>J. Org. Chem</i>. <b>58</b> (10): 2899. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00062a040">10.1021/jo00062a040</a>.</cite></span>

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<li id="cite_note-Lawrence_2001-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-Lawrence_2001_9-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFLawrence,_N.J.Crump,_J.P.McGown,_A.T.Hadfield,_J.A.2001" class="citation journal cs1">Lawrence, N.J.; Crump, J.P.; McGown, A.T.; Hadfield, J.A. (2001). "Reaction of Baylis-Hillman products with Swern and Dess-Martin oxidants". <i><a href="Tetrahedron_Lett." class="mw-redirect" title="Tetrahedron Lett.">Tetrahedron Lett.</a></i> <b>42</b> (23): <span class="nowrap">3939–</span>3941. <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%2900587-1">10.1016/S0040-4039(01)00587-1</a>.</cite></span>

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