{"id":26173,"date":"2023-01-10T15:55:01","date_gmt":"2023-01-10T21:55:01","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=26173"},"modified":"2026-04-22T10:27:23","modified_gmt":"2026-04-22T15:27:23","slug":"pinacol-rearrangement","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2023\/01\/10\/pinacol-rearrangement\/","title":{"rendered":"Pinacol Rearrangement"},"content":{"rendered":"<p><strong>The Pinacol Rearrangement<\/strong><\/p>\n<ul>\n<li>The <strong>pinacol<\/strong> <strong>rearrangement<\/strong> is an acid-catalyzed rearrangement of 1,2-diols (vicinal diols)<\/li>\n<li>The acid serves to protonate one of the hydroxyl groups, which departs as water, giving a carbocation.<\/li>\n<li>Subsequently,\u00a0 a C-O pi bond is formed as a C-C bond migrates to the adjacent carbon.<\/li>\n<li>It resembles the familiar\u00a0<strong>hydride shifts\u00a0<\/strong>and\u00a0<strong>alkyl shifts<\/strong> in that a less stable carbocation is converted to a\u00a0<strong>more stable<\/strong> carbocation (<span style=\"color: #993366;\"><em>albeit with the twist is that this &#8220;more stable carbocation&#8221; is actually the resonance form of a protonated ketone<\/em><\/span>).<\/li>\n<li>Pinacol rearrangements can result in\u00a0<strong>ring expansions<\/strong><\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-33808\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/0-summary-of-the-pinacol-rearrangement-key-example-and-mechanism.gif\" alt=\"summary of the pinacol rearrangement - key example and mechanism\" width=\"640\" height=\"447\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">The Pinacol Rearrangement<\/a><\/li>\n<li><a href=\"#two\">Mechanism of the Pinacol Rearrangement<\/a><\/li>\n<li><a href=\"#three\">Pinacol Rearrangements With Ring Expansion<\/a><\/li>\n<li><a href=\"#four\">Summary<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. The Pinacol Rearrangement<\/h2>\n<p><strong>Pinacol<\/strong> is a pleasant-smelling 1,2-diol (&#8220;vicinal&#8221; diol) with the following structure:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-33789\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/1-structure-of-the-vicinal-diol-pinacol.gif\" alt=\"structure of the vicinal diol pinacol\" width=\"642\" height=\"143\" \/><\/a><\/p>\n<p>When pinacol is treated with strong acid such as sulfuric acid (H<sub>2<\/sub>SO<sub>4<\/sub>),\u00a0 a new ketone is formed and a molecule of water is lost from the diol.\u00a0 Upon inspection, it can be seen that the carbon skeleton has undergone <strong>rearrangement<\/strong>:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-33790\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/2-example-of-pinacol-rearrangement-using-strong-acid-on-pinacol-to-give-pinacolone.gif\" alt=\"example of pinacol rearrangement using strong acid on pinacol to give pinacolone\" width=\"640\" height=\"283\" \/><\/a><\/p>\n<p>The most important thing to note here is that one of the highlighted CH<sub>3<\/sub> groups on C<sub>2<\/sub> has moved to C<sub>3<\/sub>.<\/p>\n<p>This reaction has become known as the <strong>pinacol rearrangement<\/strong>, and it is a fairly common rearrangement of 1,2-diols, having first been observed as far back as 1860. [<span style=\"color: #993366;\"><em>See <a href=\"#refone\">Ref 1<\/a><\/em><\/span>]<\/p>\n<p>It is a special case of our old friends the 1,2-hydride shift and the 1,2-alkyl shift (<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/15\/rearrangement-reactions-1-hydride-shifts\/\">Rearrangement Reactions &#8211; Hydride Shifts<\/a><\/em><\/span>)<\/p>\n<p>The reaction can be performed with a wide variety of other vicinal diols. Here is another example:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33791\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/3-example-of-pinacol-rearrangement-from-organic-syntheses-tetraphenyl-migration.gif\" alt=\"example of pinacol rearrangement from organic syntheses tetraphenyl migration\" width=\"640\" height=\"174\" \/><\/a><\/p>\n<p>In this case, a <strong>phenyl\u00a0<\/strong>group migrates to the adjacent carbon to give a new ketone adjacent to a quaternary carbon.<\/p>\n<h2><a id=\"two\"><\/a>2. Mechanism Of The Pinacol Rearrangement<\/h2>\n<p>So how does this reaction work?<\/p>\n<p>If we think back to 1,2-hydride shifts and 1,2-alkyl shifts, we&#8217;ll recall that they involve formation of a\u00a0<strong>carbocation<\/strong> followed by migration of H(-) or R(-) to generate a new carbocation. (<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/22\/rearrangement-reactions-2-alkyl-shifts\/\">Rearrangement Reactions With Alkyl Shifts<\/a><\/em><\/span>)<\/p>\n<p>So how might we generate a carbocation here from the vicinal diol and the acid?<\/p>\n<p>By protonating one of the alcohols, we generate its conjugate acid R-OH<sub>2<\/sub>(+)<\/p>\n<p>Since H<sub>2<\/sub>O is a much weaker base than HO(-), this molecule has a much better\u00a0 <strong>leaving group<\/strong>. (<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\">What Makes A Good Leaving Group?<\/a><\/em><\/span>). Breakage of the C-O bond then generates a <strong>carbocation<\/strong>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33806\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/4-first-step-of-pinacol-rearrangement-is-protonation-of-OH-and-loss-of-leaving-group-to-give-carbocation-1.gif\" alt=\"first step of pinacol rearrangement is protonation of OH and loss of leaving group to give carbocation\" width=\"640\" height=\"292\" \/><\/a><\/p>\n<p>Now, the key\u00a0<strong>rearrangement\u00a0<\/strong>step can occur, whereby a methyl group (CH<sub>3<\/sub>) can migrate from C-2 to C-3. The C<sub>2<\/sub>-CH<sub>3<\/sub> bond breaks and the C<sub>3<\/sub>-CH<sub>3<\/sub> bond forms, giving a new <strong>carbocation<\/strong>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33807\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/5-second-step-of-pinacol-rearrangement-is-migration-of-carbon-to-carbocation-resulting-in-resonance-stabilized-carbocation-1.gif\" alt=\"second step of pinacol rearrangement is migration of carbon to carbocation resulting in resonance stabilized carbocation\" width=\"640\" height=\"264\" \/><\/a><\/p>\n<p>Recall that\u00a0<strong>rearrangements\u00a0<\/strong>are generally <strong>favored<\/strong> when they result in a more <strong>stable<\/strong> carbocation. Is this true in this case?<\/p>\n<p>Actually, yes!<\/p>\n<p>If you look at the new carbocation that is formed, it can have its octet filled through donation of a lone pair by the adjacent oxygen, forming a new pi-bond in the process. (<span style=\"color: #993366;\"><em>Note: this is often called, &#8220;pi-donation&#8221; and it&#8217;s extremely important<\/em><\/span>).<\/p>\n<p>That is, this &#8220;carbocation&#8221; is actually just a\u00a0<strong>resonance form\u00a0<\/strong>of a protonated ketone!<\/p>\n<p>The final step is\u00a0<strong>deprotonation <\/strong>of the protonated ketone with a weak base to give the neutral ketone.<\/p>\n<p>That&#8217;s it.<\/p>\n<p>Although I&#8217;ve shown the reaction as proceeding stepwise, it&#8217;s also perfectly acceptable to show it as occurring in a concerted fashion. <a href=\"#noteone\">Note 1<\/a>.<\/p>\n<h2><a id=\"three\"><\/a>3. Pinacol Rearrangements With Ring Expansion<\/h2>\n<p>The pinacol rearrangement can also occur with\u00a0<strong>ring expansion<\/strong>.<\/p>\n<p>That is, pinacol rearrangements of cyclic molecules can result in the formation of larger rings.<\/p>\n<p>This is fundamentally no different from the mechanism of a typical pinacol rearrangement, but students often find them <strong>trickier<\/strong> so they end up being <strong>common exam problems<\/strong>.<\/p>\n<p>See if you can draw the key\u00a0<strong>curved arrow<\/strong> to show the rearrangement in this cyclic example:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34825\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34825\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"34825\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"34825\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34825\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34825 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34825\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-baegh\" data-id=\"baegh\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2408-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2408-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Here&#8217;s another one. Slightly different challenge. Starting with the molecule on the left, can you predict what the product of the pinacol rearrangement product on the right will be?<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34826\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34826\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"34826\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"34826\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34826\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34826 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34826\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-omgq4\" data-id=\"omgq4\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2409-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2409-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<h2><a id=\"four\"><\/a>4. Summary<\/h2>\n<ul>\n<li>The pinacol rearrangement is a special case of <strong>carbocation rearrangement<\/strong> where migration of a carbon is accompanied by formation of a new C-O (pi) bond. The product is a ketone.<\/li>\n<li>The pinacol rearrangement is promoted by the addition of <strong>acid<\/strong> which assists in loss of water as a leaving group.<\/li>\n<li>Make sure you can draw the mechanism of pinacol rearrangements that result in<strong> ring expansion<\/strong>!<\/li>\n<\/ul>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/03\/11\/3-factors-that-stabilize-carbocations\/\" class=\"\"><span>3 Factors That Stabilize Carbocations<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/22\/rearrangement-reactions-2-alkyl-shifts\/\" class=\"\"><span>Carbocation Rearrangement Reactions (2) \u2013 Alkyl Shifts<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/15\/rearrangement-reactions-1-hydride-shifts\/\" class=\"\"><span>Rearrangement Reactions (1) \u2013 Hydride Shifts<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\" class=\"\"><span>What makes a good leaving group?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/07\/the-conjugate-acid-is-a-better-leaving-group\/\" class=\"\"><span>The Conjugate Acid Is A Better Leaving Group<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/pinacol-rearrangement\/\" class=\"\"><span>Pinacol Rearrangement (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong>Note 1.<\/strong> Here is an example of showing the key rearrangement step as a concerted reaction. For more discussion on the plausibility of concerted versus stepwise pinacol rearrangements, see <a href=\"#refnine\">Ref 9<\/a>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33874\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/F1-concerted-rearrangement-step-in-the-pinacol-rearrangement.gif\" alt=\"concerted rearrangement step in the pinacol rearrangement\" width=\"640\" height=\"182\" \/><\/a><\/p>\n<p><strong>Note 2.\u00a0<\/strong>Pinacol itself is often encountered in the Suzuki reaction, since boronic esters with pinacol are highly stable and can be purified by column chromatography.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33873\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/F2-pinacolato-boronic-ester-in-suzuki-reaction.gif\" alt=\"pinacolato boronic ester in suzuki reaction\" width=\"640\" height=\"222\" \/><\/a><\/p>\n<p>For more notes on this process, see this reference from Organic Syntheses (<i>Org. Synth.<\/i>\u00a0<b>2011<\/b>,\u00a0<i>88<\/i>, 202-206\u00a0 <strong>DOI<\/strong>: <a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=v88p0202\">10.15227\/orgsyn.088.0202<\/a>)<\/p>\n<hr \/>\n<h2><strong><a id=\"quiz\"><\/a>Quiz Yourself!<\/strong><\/h2>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2410-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2411-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1817-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1920-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1932-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n<hr \/>\n<h2><strong><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/strong><\/h2>\n<ol>\n<li><strong><a id=\"refone\"><\/a>Ueber einige Producte der trockenen Destillation essigsaurer Salze<\/strong><br \/>\nR. Fittig,<br \/>\n<em>Annalen<\/em>, 1859, 110, 17, 23; 1860, 114, 54.<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/doi.org\/10.1002\/jlac.18591100103\">10.1002\/jlac.18591100103<\/a><br \/>\nOriginal reports on what would come to be called the Pinacol Rearrangement.<\/li>\n<li><strong>PINACOLONE<br \/>\n<\/strong> A. Hill and E. W. Flosdorf<br \/>\n<em>Org. Synth.<\/em> <strong>1925<\/strong>, <em>5<\/em>, 91<br \/>\n<strong>DOI: <\/strong><a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=CV1P0462\">10.15227\/orgsyn.005.0091<\/a><br \/>\nReproducible and tested experimental procedure for the pinacol-pinacolone rearrangement in <em>Organic Syntheses.<\/em><\/li>\n<li><strong>The Pinacol Rearrangement<\/strong><br \/>\nClair J. Collins<br \/>\n<em>Quarterly Reviews of the Chemical Society<\/em>,\u00a0<strong>1960<\/strong>,\u00a0<em>14, <\/em>357-377<br \/>\n<strong>DOI: <\/strong><a class=\"text--small\" title=\"Link to landing page via DOI\" href=\"https:\/\/doi.org\/10.1039\/QR9601400357\">10.1039\/QR9601400357<\/a><br \/>\nReview on the pinacol rearrangement covering the older literature.<\/li>\n<li><strong>Internally competitive methyl vs. methyl-d3 migration and kinetic isotope effects. Means of determining whether or not methyl migration occurs in the rate-controlling step<\/strong><br \/>\nW. M. Schubert and Paul H. LeFevre<br \/>\n<cite>Journal of the American Chemical Society<\/cite>\u00a0<strong>1972<\/strong>\u00a0<em>94<\/em>\u00a0(5), 1639-1645<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja00760a035\">10.1021\/ja00760a035<\/a><br \/>\nThe authors find a significant kinetic isotope effect for the migration of CH3 vs CD3 (1.232) in the pinacol rearrangement, indicating that alkyl migration is the rate-determining step after a (reversible) C-O bond-breaking step.<\/li>\n<li><strong>What Is a Discovery? Carbon Skeletal Rearrangements as Counter\u2010Examples to the Rule of Minimal Structural Change<\/strong><br \/>\nJerome A. Berson<br \/>\n<em>Angewandte Chemie International Edition<\/em> <strong>2002<\/strong> <em>41<\/em> (24), 4655-4660<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/full\/10.1002\/anie.200290007\">1002\/anie.200290007<\/a><br \/>\nThis article provides a historical perspective on the discovery of the pinacol rearrangement, including the mistakes that were made in characterizing the products and also includes references to old papers (1850\u2019s and earlier) on the topic.<\/li>\n<li>\n<p class=\"capsule__title fixpadv--m\"><strong>Stereochemical fate of an asymmetric migrating group in the pinacol rearrangement<br \/>\n<\/strong>J. J. Beggs and M. B. Meyers<br \/>\n<em>J. Chem. Soc. B<\/em>\u00a0<strong>1970<\/strong>, 930-934<br \/>\n<strong>DOI: <\/strong><a class=\"text--small\" title=\"Link to landing page via DOI\" href=\"https:\/\/doi.org\/10.1039\/J29700000930\">10.1039\/J29700000930<\/a><br \/>\nThe authors study the pinacol rearrangement of a chiral diol and finds that migration of a chiral alkyl fragment does not result in the loss of optical activity, indicating that it proceeded with retention of configuration.<\/p>\n<\/li>\n<li><strong>The Pinacol\u2014Pinacolone Rearrangement. VI. The Rearrangement of Symmetrical Aromatic Pinacols<\/strong><br \/>\nW. E. Bachmann and James W. Ferguson<br \/>\n<cite>Journal of the American Chemical Society<\/cite>\u00a0<strong>1934<\/strong>\u00a0<em>56<\/em> (10), 2081-2084<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja01325a023\">10.1021\/ja01325a023<\/a><br \/>\nVery interesting study on a series of symmetrical aromatic pinacols R1R2C(OH)(HO)CR2R1 to investigate relative migratory aptitudes. Aromatic groups with\u00a0<em>p-<\/em>alkoxy groups had the highest migratory aptitudes; <em>o-<\/em>halophenyls had the lowest.<\/li>\n<li><strong>Single Stereodifferentiation Associated with Carbon Atom Insertion during the Oxonium Ion-Initiated Pinacol Rearrangement of Dihydrofuranyl and Dihydropyranyl Carbinols<br \/>\n<\/strong>Leo A. Paquette, James C. Lanter, and Jeffrey N. Johnston<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em> <strong>1997<\/strong> <em>62<\/em> (6), 1702-1712<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo962019j\">10.1021\/jo962019j<\/a><br \/>\nProf. Leo Paquette demonstrates that stereodifferentiation is possible in pinacol-type rearrangements.<\/li>\n<li><strong><a id=\"refnine\"><\/a>Theoretical study of the reaction mechanism and migratory aptitude of the pinacol rearrangement<\/strong>\n<div>Kensuke Nakamura and Yoshihiro Osamura<\/div>\n<div><cite>Journal of the American Chemical Society<\/cite>\u00a0<strong>1993<\/strong>\u00a0<em>115<\/em> (20), 9112-9120<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja00073a029\">10.1021\/ja00073a029<\/a><br \/>\nThis theoretical study evaluates both concerted and stepwise pathways for the pinacol rearrangement proposes that the pinacol rearrangement proceeds through a concerted mechanism in non-ionizing solvents.<\/div>\n<\/li>\n<li><strong>Dynamic Effects on Migratory Aptitudes in Carbocation Reactions<br \/>\n<\/strong>Zhitao Feng and Dean J. Tantillo<br \/>\n<cite>Journal of the American Chemical Society<\/cite>\u00a0<strong>2021<\/strong>\u00a0<em>143<\/em>\u00a0(2), 1088-1097<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/full\/10.1021\/jacs.0c11850\">10.1021\/jacs.0c11850<\/a><br \/>\nTheoretical study on migratory aptitudes in carbocation rearrangement reactions.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>The Pinacol Rearrangement The pinacol rearrangement is an acid-catalyzed rearrangement of 1,2-diols (vicinal diols) The acid serves to protonate one of the hydroxyl groups, which <\/p>\n","protected":false},"author":1,"featured_media":33808,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1416],"tags":[864,860,466,14817,859,14818,468],"post_folder":[],"class_list":["post-26173","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-rearrangements","tag-alkyl-shift","tag-carbocation","tag-diols","tag-pinacol","tag-rearrangement","tag-vicinal-diol","tag-wagner-meerwein"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Pinacol Rearrangement &#8211; 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