<!DOCTYPE html>
<html class="client-nojs vector-feature-night-mode-disabled vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-sticky-header-enabled" lang="en" dir="ltr"><head>
<meta charset="UTF-8">
<title>Dess–Martin oxidation</title>
<meta name="viewport" content="width=device-width, initial-scale=1.0">
<link rel="canonical" href="https://en.wikipedia.org/wiki/Dess%E2%80%93Martin_oxidation"> <link href="./mw/ext.cite.styles.css" rel="stylesheet" type="text/css">
<link href="./mw/skins.vector.icons.css" rel="stylesheet" type="text/css">
<link href="./mw/skins.vector.search.codex.styles.css" rel="stylesheet" type="text/css">
<link href="./mw/skins.vector.styles.css" rel="stylesheet" type="text/css">
<link href="./mw/user.styles.css" rel="stylesheet" type="text/css">
<meta name="ResourceLoaderDynamicStyles" content="">
<link rel="stylesheet" type="text/css" href="./mw/site.styles.css">
<link rel="stylesheet" type="text/css" href="./mw/noscript.css">
<link rel="stylesheet" type="text/css" href="./footer.css">
<link rel="stylesheet" type="text/css" href="./vector-2022.css">
</head>
<body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject page-Dess–Martin_oxidation rootpage-Dess–Martin_oxidation skin-vector-2022 action-view">
<div class="mw-page-container">
<div class="mw-page-container-inner">
<div class="mw-content-container">
<main id="content" class="mw-body">
<header class="mw-body-header vector-page-titlebar">
<h1 id="firstHeading" class="firstHeading mw-first-heading">
<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Dess–Martin oxidation</span></span>
</h1>
</header>
<a id="top"></a>
<div id="bodyContent" class="vector-body ve-init-mw-desktopArticleTarget-targetContainer" aria-labelledby="firstHeading" data-mw-ve-target-container="">
<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="en" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr">
<style data-mw-deduplicate="TemplateStyles:r1236090951">
/* 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">This article is about the oxidation reaction. For the oxidizing reagent, see <a href="Dess%E2%80%93Martin_periodinane" title="Dess–Martin periodinane">Dess–Martin periodinane</a>.</div>
<style data-mw-deduplicate="TemplateStyles:r1049416944">
/* start https://en.wikipedia.org/ */
.mw-parser-output .ib-reactionbox{border-collapse:collapse}.mw-parser-output .ib-reactionbox td,.mw-parser-output .ib-reactionbox th{border:1px solid #a2a9b1}
/* end https://en.wikipedia.org/ */
</style>
<table class="infobox ib-reactionbox">
<tbody><tr>
<th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Dess–Martin oxidation
</th></tr>
<tr>
<td>Named after
</td>
<td>Daniel Benjamin Dess <br> <a href="James_Cullen_Martin" title="James Cullen Martin">James Cullen Martin</a>
</td></tr>
<tr>
<td>Reaction type
</td>
<td><a href="Organic_redox_reaction" title="Organic redox reaction">Organic redox reaction</a>
</td></tr>
<tr>
<th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Identifiers
</th></tr>
<tr>
<td>Organic Chemistry Portal
</td>
<td><span class="reflink nourlexpansion"><a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/namedreactions/dess-martin-oxidation.shtm">dess-martin-oxidation</a></span>
</td></tr>
<tr>
<td><a href="Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a> ontology ID
</td>
<td><span class="reflink nourlexpansion"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/ols/ontologies/rxno/terms?iri=http%3A%2F%2Fpurl.obolibrary.org%2Fobo%2FRXNO_0000256">RXNO:0000256</a></span>
</td></tr>
<tr>
<td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">
</td></tr>
</tbody></table>
<p>The <b>Dess–Martin oxidation</b> is an <a href="Organic_reaction" title="Organic reaction">organic reaction</a> for the <a href="Redox" title="Redox">oxidation</a> of primary <a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> to <a href="Aldehyde" title="Aldehyde">aldehydes</a> and secondary alcohols to <a href="Ketone" title="Ketone">ketones</a> using <a href="Dess%E2%80%93Martin_periodinane" title="Dess–Martin periodinane">Dess–Martin periodinane</a>.<sup id="cite_ref-Dess83_1-0" class="reference"><a href="#cite_note-Dess83-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Carey_2-0" class="reference"><a href="#cite_note-Carey-2"><span class="cite-bracket">[</span>2<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 periodinane reagent in 1983.
</p><p>The reaction uses a <a href="Hypervalent_iodine" class="mw-redirect" title="Hypervalent iodine">hypervalent iodine</a> reagent<sup id="cite_ref-Carey_2-1" class="reference"><a href="#cite_note-Carey-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> similar to <a href="2-iodoxybenzoic_acid" class="mw-redirect" title="2-iodoxybenzoic acid">2-iodoxybenzoic acid</a> to selectively and mildly oxidize alcohols to aldehydes or ketones. The reaction is commonly conducted in chlorinated solvents such as <a href="Dichloromethane" title="Dichloromethane">dichloromethane</a> or <a href="Chloroform" title="Chloroform">chloroform</a>.<sup id="cite_ref-Carey_2-2" class="reference"><a href="#cite_note-Carey-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The reaction can be done at room temperature and is quickly complete. Many other functional groups will not be affected by this reaction.
</p>
<p>The Dess–Martin oxidation may be preferable to other oxidation reactions as it is very mild, avoids the use of toxic <a href="Chromium" title="Chromium">chromium</a> reagents, does not require large excess or co-oxidants, and has a relatively easy workup.
</p>
<dl><dd></dd></dl>
<p>The reaction produces two equivalents of <a href="Acetic_acid" title="Acetic acid">acetic acid</a>. It can be buffered with <a href="Pyridine" title="Pyridine">pyridine</a> or <a href="Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a> in order to protect acid-labile compounds.
</p><p>The rate of oxidation can be increased by the addition of water to the reaction mixture.<sup id="cite_ref-Meyer94_3-0" class="reference"><a href="#cite_note-Meyer94-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>
<style data-mw-deduplicate="TemplateStyles:r1239543626">
/* 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">
<div class="mw-references-wrap"><ol class="references">
<li id="cite_note-Dess83-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Dess83_1-0">^</a></b></span> <span class="reference-text"><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><cite id="CITEREFDessMartin1983" class="citation journal cs1">Dess, Daniel B.; <a href="James_Cullen_Martin" title="James Cullen Martin">Martin, James Cullen</a> (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-Carey-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Carey_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Carey_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Carey_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><cite id="Carey" class="citation book cs1">Carey, Francis A.; Sundberg, Richard J. (2007). <i>Advanced Organic Chemistry: Part B: Reactions and Synthesis</i> (5th ed.). New York: Springer. p. 1072. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0387683546</bdi>.</cite></span>
</li>
<li id="cite_note-Meyer94-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Meyer94_3-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFMeyerSchreiber1994" class="citation journal cs1">Meyer, Stephanie D.; <a href="Stuart_Schreiber" title="Stuart Schreiber">Schreiber, Stuart L.</a> (1994). "Acceleration of the Dess-Martin Oxidation by Water". <i><a href="J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a></i> <b>59</b> (24): <span class="nowrap">7549–</span>7552. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00103a067">10.1021/jo00103a067</a>.</cite></span>
</li>
</ol></div></div>
</div><!--htdig_noindex--><div><div class="zim-footer">
This article is issued from <a class="external text" title="Last edited on 2025-05-17" href="https://en.wikipedia.org/wiki/?title=Dess%E2%80%93Martin_oxidation&oldid=1290923490">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><!--/htdig_noindex--></div>
</div>
</main>
</div>
</div>
</div>
</body></html>