CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-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-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Aromatization - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-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-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy", "wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"36940032-5873-4b87-8a5a-cafbd096fe45","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Aromatization","wgTitle":"Aromatization","wgCurRevisionId":1256231057,"wgRevisionId":1256231057,"wgArticleId":2199220,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["CS1 German-language sources (de)","Articles with short description","Short description is different from Wikidata","Hydrogen","Oil refining","Organic redox reactions"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Aromatization","wgRelevantArticleId":2199220,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[],"wgNoticeProject":"wikipedia", "wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":10000,"wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q698026","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGEStructuredTaskRejectionReasonTextInputEnabled":false, "wgGELevelingUpEnabledForUser":false};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents", "ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.growthExperiments.SuggestedEditSession","wikibase.sidebar.tracking"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Aromatization - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Aromatization"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Aromatization&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Aromatization"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="//login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Aromatization rootpage-Aromatization skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Aromatization" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Aromatization" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Aromatization" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Aromatization" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Industrial_practice" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Industrial_practice"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Industrial practice</span> </div> </a> <ul id="toc-Industrial_practice-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biochemical_processes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biochemical_processes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Biochemical processes</span> </div> </a> <ul id="toc-Biochemical_processes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory_methods" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Laboratory_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Laboratory methods</span> </div> </a> <button aria-controls="toc-Laboratory_methods-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Laboratory methods subsection</span> </button> <ul id="toc-Laboratory_methods-sublist" class="vector-toc-list"> <li id="toc-Oxidative_dehydrogenation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidative_dehydrogenation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Oxidative dehydrogenation</span> </div> </a> <ul id="toc-Oxidative_dehydrogenation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dehydration" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dehydration"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Dehydration</span> </div> </a> <ul id="toc-Dehydration-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tautomerization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Tautomerization"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Tautomerization</span> </div> </a> <ul id="toc-Tautomerization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydride_and_proton_abstraction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydride_and_proton_abstraction"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Hydride and proton abstraction</span> </div> </a> <ul id="toc-Hydride_and_proton_abstraction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_acyclic_precursors" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_acyclic_precursors"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>From acyclic precursors</span> </div> </a> <ul id="toc-From_acyclic_precursors-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Aromatization</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 12 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-12" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">12 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%B1%D9%85%D8%AA%D8%A9" title="أرمتة – Arabic" lang="ar" hreflang="ar" data-title="أرمتة" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Aromatizace" title="Aromatizace – Czech" lang="cs" hreflang="cs" data-title="Aromatizace" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Aromatisierung_(Chemie)" title="Aromatisierung (Chemie) – German" lang="de" hreflang="de" data-title="Aromatisierung (Chemie)" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Aromatizaci%C3%B3n" title="Aromatización – Spanish" lang="es" hreflang="es" data-title="Aromatización" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D8%B1%D9%88%D9%85%D8%A7%D8%AA%DB%8C%DA%A9%E2%80%8C%D8%B4%D8%AF%D9%86" title="آروماتیک‌شدن – Persian" lang="fa" hreflang="fa" data-title="آروماتیک‌شدن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Aromatisation" title="Aromatisation – French" lang="fr" hreflang="fr" data-title="Aromatisation" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Aromatizaci%C3%B3n" title="Aromatización – Galician" lang="gl" hreflang="gl" data-title="Aromatización" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B0%A9%ED%96%A5%EC%A1%B1%ED%99%94" title="방향족화 – Korean" lang="ko" hreflang="ko" data-title="방향족화" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D6%80%D5%B8%D5%B4%D5%A1%D5%BF%D5%A1%D6%81%D5%B8%D6%82%D5%B4" title="Արոմատացում – Armenian" lang="hy" hreflang="hy" data-title="Արոմատացում" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Aromatisasi" title="Aromatisasi – Malay" lang="ms" hreflang="ms" data-title="Aromatisasi" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Aromatiza%C3%A7%C3%A3o" title="Aromatização – Portuguese" lang="pt" hreflang="pt" data-title="Aromatização" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D1%80%D0%BE%D0%BC%D0%B0%D1%82%D0%B8%D0%B7%D0%B0%D1%86%D1%96%D1%8F" title="Ароматизація – Ukrainian" lang="uk" hreflang="uk" data-title="Ароматизація" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q698026#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Aromatization" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Aromatization" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">English</span> </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Aromatization"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Aromatization&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Aromatization&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Tools</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Aromatization"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Aromatization&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Aromatization&action=history"><span>View history</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Aromatization" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Aromatization" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q"><span>Special pages</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Aromatization&oldid=1256231057" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Aromatization&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Aromatization&id=1256231057&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FAromatization"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FAromatization"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Aromatization&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Aromatization&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q698026" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical reaction</div> <p><b>Aromatization</b> is a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> in which an <a href="/wiki/Aromaticity" title="Aromaticity">aromatic system</a> is formed from a single nonaromatic precursor. Typically aromatization is achieved by dehydrogenation of existing cyclic compounds, illustrated by the conversion of <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> into <a href="/wiki/Benzene" title="Benzene">benzene</a>. Aromatization includes the formation of heterocyclic systems.<sup id="cite_ref-March_1-0" class="reference"><a href="#cite_note-March-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:MeC6H11toPhMe.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/MeC6H11toPhMe.png/422px-MeC6H11toPhMe.png" decoding="async" width="422" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/MeC6H11toPhMe.png/633px-MeC6H11toPhMe.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/MeC6H11toPhMe.png/844px-MeC6H11toPhMe.png 2x" data-file-width="1277" data-file-height="298" /></a><figcaption>The conversion of <a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">methylcyclohexane</a> to <a href="/wiki/Toluene" title="Toluene">toluene</a> is a classic aromatization reaction. This platinum (Pt)-catalyzed process is practiced on scale in the production of <a href="/wiki/Gasoline" title="Gasoline">gasoline</a> from petroleum.</figcaption></figure></dd></dl> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Industrial_practice">Industrial practice</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=1" title="Edit section: Industrial practice"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although not practiced under the name, aromatization is a cornerstone of <a href="/wiki/Oil_refining" class="mw-redirect" title="Oil refining">oil refining</a>. One of the major reforming reactions is the <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenation</a> of <a href="/wiki/Alkane" title="Alkane">paraffins</a> and <a href="/wiki/Cycloalkane" title="Cycloalkane">naphthenes</a> into aromatics. </p><p>The process, which is catalyzed by platinum supported by aluminium oxide, is exemplified in the conversion <a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">methylcyclohexane</a> (a naphthene) into <a href="/wiki/Toluene" title="Toluene">toluene</a> (an aromatic).<sup id="cite_ref-Gary_2-0" class="reference"><a href="#cite_note-Gary-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> <b>Dehydrocyclization</b> converts paraffins (acyclic hydrocarbons) into aromatics.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> A related aromatization process includes <b>dehydroisomerization</b> of <a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">methylcyclopentane</a> to benzene: </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:MeC5H9toPhH.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/MeC5H9toPhH.png/342px-MeC5H9toPhH.png" decoding="async" width="342" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/MeC5H9toPhH.png/513px-MeC5H9toPhH.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/MeC5H9toPhH.png/684px-MeC5H9toPhH.png 2x" data-file-width="1118" data-file-height="273" /></a><figcaption></figcaption></figure></dd></dl> <p>As of alkanes, they first dehydrogenate to olefins, then <a href="/wiki/Cyclization" class="mw-redirect" title="Cyclization">form rings</a> at the place of the double bond, becoming cycloalkanes, and finally gradually lose hydrogen to become aromatic hydrocarbons.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>For cyclohexane, cyclohexene, and cyclohexadiene, dehydrogenation is the conceptually simplest pathway for aromatization. The activation barrier decreases with the degree of unsaturation. Thus, cyclohexadienes are especially prone to aromatization. Formally, dehydrogenation is a <a href="/wiki/Redox" title="Redox">redox</a> process. Dehydrogenative aromatization is the reverse of arene hydrogenation. As such, hydrogenation catalysts are effective for the reverse reaction. Platinum-catalyzed dehydrogenations of cyclohexanes and related feedstocks are the largest scale applications of this reaction (see above).<sup id="cite_ref-March_1-1" class="reference"><a href="#cite_note-March-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biochemical_processes">Biochemical processes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=2" title="Edit section: Biochemical processes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Testosterone_estradiol_conversion.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Testosterone_estradiol_conversion.png/400px-Testosterone_estradiol_conversion.png" decoding="async" width="400" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Testosterone_estradiol_conversion.png/600px-Testosterone_estradiol_conversion.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/72/Testosterone_estradiol_conversion.png/800px-Testosterone_estradiol_conversion.png 2x" data-file-width="4539" data-file-height="1531" /></a><figcaption></figcaption></figure></dd></dl> <p><a href="/wiki/Aromatase" title="Aromatase">Aromatases</a> are <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> that aromatize rings within steroids. The specific conversions are <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> to <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> and <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a> to <a href="/wiki/Estrone" title="Estrone">estrone</a>.<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> Each of these aromatizations involves the oxidation of the C-19 <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> group to allow for the elimination of <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a> concomitant with aromatization. Such conversions are relevant to estrogen <a href="/wiki/Tumorogenesis" class="mw-redirect" title="Tumorogenesis">tumorogenesis</a> in the development of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> and <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</a> in <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women and <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> in men.<sup id="cite_ref-MedChem_6-0" class="reference"><a href="#cite_note-MedChem-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Aromatase_inhibitors" class="mw-redirect" title="Aromatase inhibitors">Aromatase inhibitors</a> like <a href="/wiki/Exemestane" title="Exemestane">exemestane</a> (which forms a permanent and deactivating bond with the aromatase enzyme)<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> and <a href="/wiki/Anastrozole" title="Anastrozole">anastrozole</a> and <a href="/wiki/Letrozole" title="Letrozole">letrozole</a> (which <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">compete</a> for the enzyme)<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> have been shown to be more effective than anti-estrogen medications such as <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a> likely because they prevent the formation of estradiol.<sup id="cite_ref-MedChem_6-1" class="reference"><a href="#cite_note-MedChem-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Laboratory_methods">Laboratory methods</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=3" title="Edit section: Laboratory methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although practiced on a very small scale compared to the petrochemical routes, diverse methods have been developed for fine chemical syntheses. </p> <div class="mw-heading mw-heading3"><h3 id="Oxidative_dehydrogenation">Oxidative dehydrogenation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=4" title="Edit section: Oxidative dehydrogenation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/2,3-Dichloro-5,6-dicyano-1,4-benzoquinone" title="2,3-Dichloro-5,6-dicyano-1,4-benzoquinone">2,3-Dichloro-5,6-dicyano-1,4-benzoquinone</a> (DDQ) is often the reagent of choice. DDQ and an acid catalyst has been used to synthesise a steroid with a <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a> core by oxidation accompanied by a double <a href="/wiki/Methyl_migration" class="mw-redirect" title="Methyl migration">methyl migration</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In the process, DDQ is itself reduced into an aromatic <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a> product. </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:DDQ_aromatization_rearrangement.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/DDQ_aromatization_rearrangement.png/500px-DDQ_aromatization_rearrangement.png" decoding="async" width="500" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/DDQ_aromatization_rearrangement.png/750px-DDQ_aromatization_rearrangement.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/DDQ_aromatization_rearrangement.png/1000px-DDQ_aromatization_rearrangement.png 2x" data-file-width="2625" data-file-height="702" /></a><figcaption></figcaption></figure></dd></dl> <p>Sulfur and selenium are traditionally used in aromatization, the leaving group being <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Soluble transition metal complexes can induce oxidative aromatization concomitant with complexation. <a href="/wiki/Phellandrene" title="Phellandrene">α-Phellandrene</a> (2-methyl-5-<i>iso</i>-propyl-1,3-cyclohexadiene) is oxidised to <a href="/wiki/P-cymene" class="mw-redirect" title="P-cymene"><i>p</i>-<i>iso</i>-propyltoluene</a> with the reduction of <a href="/wiki/Ruthenium_trichloride" class="mw-redirect" title="Ruthenium trichloride">ruthenium trichloride</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Oxidative dehydrogenation of dihydropyridine results in aromatization, giving <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Dehydration">Dehydration</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=5" title="Edit section: Dehydration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Semmler-Wolff_reaction.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Semmler-Wolff_reaction.svg/220px-Semmler-Wolff_reaction.svg.png" decoding="async" width="220" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Semmler-Wolff_reaction.svg/330px-Semmler-Wolff_reaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Semmler-Wolff_reaction.svg/440px-Semmler-Wolff_reaction.svg.png 2x" data-file-width="235" data-file-height="118" /></a><figcaption>240pxSemmler-Wolff synthesis of <a href="/wiki/Aniline" title="Aniline">aniline</a> </figcaption></figure> <p>Non-aromatic rings can be aromatized in many ways. <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">Dehydration</a> allows the <a href="/wiki/Semmler-Wolff_reaction" class="mw-redirect" title="Semmler-Wolff reaction">Semmler-Wolff reaction</a> of <a href="/wiki/2-cyclohexenone" class="mw-redirect" title="2-cyclohexenone">2-cyclohexenone</a> <a href="/wiki/Oxime" title="Oxime">oxime</a> to <a href="/wiki/Aniline" title="Aniline">aniline</a> under acidic conditions.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Tautomerization">Tautomerization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=6" title="Edit section: Tautomerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Tetrahydronaphthalenedione.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Tetrahydronaphthalenedione.png/280px-Tetrahydronaphthalenedione.png" decoding="async" width="280" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Tetrahydronaphthalenedione.png/420px-Tetrahydronaphthalenedione.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Tetrahydronaphthalenedione.png/560px-Tetrahydronaphthalenedione.png 2x" data-file-width="1480" data-file-height="692" /></a><figcaption>1,4-Dioxotetralin and its aromatized tautomer 1,4-naphthalenediol coexist in equal abundance in solution.</figcaption></figure> <p>The <a href="/wiki/Isomerization" title="Isomerization">isomerization</a> of cyclohexadienones gives the aromatic tautomer <a href="/wiki/Phenol" title="Phenol">phenol</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Isomerization of 1,4-naphthalenediol at 200 °C produces a 2:1 mixture with its keto form, 1,4-dioxotetralin.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hydride_and_proton_abstraction">Hydride and proton abstraction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=7" title="Edit section: Hydride and proton abstraction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Classically, aromatization reactions involve changing the C:H ratio of a substrate. When applied to <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a>, proton removal gives the aromatic conjugate base <a href="/wiki/Cyclopentadienyl_anion" title="Cyclopentadienyl anion">cyclopentadienyl anion</a>, isolable as <a href="/wiki/Sodium_cyclopentadienide" title="Sodium cyclopentadienide">sodium cyclopentadienide</a>:<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>2 Na + 2 C<sub>5</sub>H<sub>6</sub> → 2 NaC<sub>5</sub>H<sub>5</sub> + <a href="/wiki/Hydrogen" title="Hydrogen">H<sub>2</sub></a></dd></dl> <p>Aromatization can entail removal of hydride. Tropylium, <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">7</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">7</sub></span></span></span> arises by the aromatization reaction of cycloheptatriene with hydride acceptors. </p> <dl><dd><span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">7</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">8</sub></span></span></span> + <span class="chemf nowrap">Br<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> → <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">7</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">7</sub></span></span></span> + <span class="chemf nowrap">Br<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span> + <span class="chemf nowrap">HBr</span></dd></dl> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ciamician-Dennstedt_Rearrangement.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Ciamician-Dennstedt_Rearrangement.png/400px-Ciamician-Dennstedt_Rearrangement.png" decoding="async" width="400" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Ciamician-Dennstedt_Rearrangement.png/600px-Ciamician-Dennstedt_Rearrangement.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/56/Ciamician-Dennstedt_Rearrangement.png/800px-Ciamician-Dennstedt_Rearrangement.png 2x" data-file-width="3780" data-file-height="540" /></a><figcaption><a href="/wiki/Pyrrole#Cyclization_reactions" title="Pyrrole">Ciamician-Dennstedt rearrangement</a> of a pyrrole to a pyridine. The first step involves <b>dearomatization</b>. The second step involves aromatization.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="From_acyclic_precursors">From acyclic precursors</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=8" title="Edit section: From acyclic precursors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The aromatization of acyclic precursors is rarer in organic synthesis, although it is a significant component of the <a href="/wiki/BTX_(chemistry)" title="BTX (chemistry)">BTX production</a> in refineries. </p><p>Among acyclic precursors, alkynes are relatively prone to aromatizations since they are partially dehydrogenated. The <a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a> converts an <a href="/wiki/Enediyne" title="Enediyne">enediyne</a> to a dehydrobenzene intermediate diradical, which abstracts hydrogen to aromatize.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The enediyne moiety can be included within an existing ring, allowing access to a bicyclic system under mild conditions as a consequence of the <a href="/wiki/Ring_strain" title="Ring strain">ring strain</a> in the reactant. Cyclodeca-3-en-1,5-diyne reacts with <a href="/wiki/1,3-cyclohexadiene" class="mw-redirect" title="1,3-cyclohexadiene">1,3-cyclohexadiene</a> to produce benzene and <a href="/wiki/Tetralin" title="Tetralin">tetralin</a> at 37 °C, the reaction being highly favorable owing to the formation of two new aromatic rings: </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Bergman_cyclization.svg" class="mw-file-description" title="Scheme 1. Bergman cyclization"><img alt="Scheme 1. Bergman cyclization" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Bergman_cyclization.svg/500px-Bergman_cyclization.svg.png" decoding="async" width="500" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Bergman_cyclization.svg/750px-Bergman_cyclization.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Bergman_cyclization.svg/1000px-Bergman_cyclization.svg.png 2x" data-file-width="1110" data-file-height="345" /></a><figcaption>Scheme 1. Bergman cyclization</figcaption></figure></dd></dl> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Aromatase" title="Aromatase">Aromatase</a></li> <li><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic hydrocarbon</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aromatization&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.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}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-March-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-March_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.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("//upload.wikimedia.org/wikipedia/commons/6/65/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("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/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}}</style><cite id="CITEREFSmith,_Michael_B.March,_Jerry2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.au=Smith%2C+Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-Gary-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Gary_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGary,_J.H.Handwerk,_G.E.1984" class="citation book cs1">Gary, J.H.; Handwerk, G.E. (1984). <i>Petroleum Refining Technology and Economics</i> (2nd ed.). Marcel Dekker, Inc. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-8247-7150-8" title="Special:BookSources/0-8247-7150-8"><bdi>0-8247-7150-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Petroleum+Refining+Technology+and+Economics&rft.edition=2nd&rft.pub=Marcel+Dekker%2C+Inc&rft.date=1984&rft.isbn=0-8247-7150-8&rft.au=Gary%2C+J.H.&rft.au=Handwerk%2C+G.E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOno,_Y.1992" class="citation journal cs1">Ono, Y. (1992). "Transformation of Lower Alkanes into Aromatic Hydrocarbons over ZSM-5 Zeolites". <i>Catal. Rev. - Sci. Eng</i>. <b>34</b> (3): 179–226. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F01614949208020306">10.1080/01614949208020306</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Catal.+Rev.+-+Sci.+Eng.&rft.atitle=Transformation+of+Lower+Alkanes+into+Aromatic+Hydrocarbons+over+ZSM-5+Zeolites.&rft.volume=34&rft.issue=3&rft.pages=179-226&rft.date=1992&rft_id=info%3Adoi%2F10.1080%2F01614949208020306&rft.au=Ono%2C+Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOxtobyGillisButler2016" class="citation book cs1">Oxtoby, David W.; Gillis, H. Pat; Butler, Laurie J. (2016-01-01). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IQGEDwAAQBAJ&pg=PA302"><i>Principles of Modern Chemistry</i></a>. Cengage AU. p. 302. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-305-07911-3" title="Special:BookSources/978-1-305-07911-3"><bdi>978-1-305-07911-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+Modern+Chemistry&rft.pages=302&rft.pub=Cengage+AU&rft.date=2016-01-01&rft.isbn=978-1-305-07911-3&rft.aulast=Oxtoby&rft.aufirst=David+W.&rft.au=Gillis%2C+H.+Pat&rft.au=Butler%2C+Laurie+J.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DIQGEDwAAQBAJ%26pg%3DPA302&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLephart,_E._D.1996" class="citation journal cs1">Lephart, E. D. (1996). "A Review of Brain Aromatase Cytochrome P450". <i>Brain Res. Rev</i>. <b>22</b> (1): 1–26. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0165-0173%2896%2900002-1">10.1016/0165-0173(96)00002-1</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8871783">8871783</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:11987113">11987113</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Brain+Res.+Rev.&rft.atitle=A+Review+of+Brain+Aromatase+Cytochrome+P450&rft.volume=22&rft.issue=1&rft.pages=1-26&rft.date=1996&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11987113%23id-name%3DS2CID&rft_id=info%3Apmid%2F8871783&rft_id=info%3Adoi%2F10.1016%2F0165-0173%2896%2900002-1&rft.au=Lephart%2C+E.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-MedChem-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-MedChem_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MedChem_6-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAvendañoMenéndez2008" class="citation book cs1">Avendaño, C.; Menéndez, J. C. (2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=GjhXyqB5iLcC&q=aromatase+testosterone+estradiol&pg=PA66">"Aromatase Inhibitors"</a>. <i>Medicinal Chemistry of Anticancer Drugs</i>. <a href="/wiki/Elsevier" title="Elsevier">Elsevier</a>. pp. 65–73. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-444-52824-7.00003-2">10.1016/B978-0-444-52824-7.00003-2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780080559629" title="Special:BookSources/9780080559629"><bdi>9780080559629</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Aromatase+Inhibitors&rft.btitle=Medicinal+Chemistry+of+Anticancer+Drugs&rft.pages=65-73&rft.pub=Elsevier&rft.date=2008&rft_id=info%3Adoi%2F10.1016%2FB978-0-444-52824-7.00003-2&rft.isbn=9780080559629&rft.aulast=Avenda%C3%B1o&rft.aufirst=C.&rft.au=Men%C3%A9ndez%2C+J.+C.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGjhXyqB5iLcC%26q%3Daromatase%2Btestosterone%2Bestradiol%26pg%3DPA66&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJasek2007" class="citation book cs1 cs1-prop-foreign-lang-source">Jasek, W., ed. (2007). <i>Austria-Codex</i> (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 656–660. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783852001814" title="Special:BookSources/9783852001814"><bdi>9783852001814</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Austria-Codex&rft.place=Vienna&rft.pages=656-660&rft.edition=62nd&rft.pub=%C3%96sterreichischer+Apothekerverlag&rft.date=2007&rft.isbn=9783852001814&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDinnendahlFricke2007" class="citation book cs1 cs1-prop-foreign-lang-source">Dinnendahl, V.; Fricke, U., eds. (2007). <i>Arzneistoff-Profile</i> (in German). Vol. 4 (21st ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783774198463" title="Special:BookSources/9783774198463"><bdi>9783774198463</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Arzneistoff-Profile&rft.place=Eschborn%2C+Germany&rft.edition=21st&rft.pub=Govi+Pharmazeutischer+Verlag&rft.date=2007&rft.isbn=9783774198463&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBrownTurner1971" class="citation journal cs1">Brown, W.; Turner, A. B. (1971). "Applications of High-Potential Quinones. Part VII. The Synthesis of Steroidal Phenanthrenes by Double Methyl Migration". <i><a href="/wiki/Journal_of_the_Chemical_Society_C:_Organic" class="mw-redirect" title="Journal of the Chemical Society C: Organic">Journal of the Chemical Society C: Organic</a></i>. <b>14</b>: 2566–2572. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FJ39710002566">10.1039/J39710002566</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5167256">5167256</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society+C%3A+Organic&rft.atitle=Applications+of+High-Potential+Quinones.+Part+VII.+The+Synthesis+of+Steroidal+Phenanthrenes+by+Double+Methyl+Migration&rft.volume=14&rft.pages=2566-2572&rft.date=1971&rft_id=info%3Adoi%2F10.1039%2FJ39710002566&rft_id=info%3Apmid%2F5167256&rft.aulast=Brown&rft.aufirst=W.&rft.au=Turner%2C+A.+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBergmannSzmuszkowiczFawaz1947" class="citation journal cs1">Bergmann, F.; Szmuszkowicz, J.; Fawaz, G. (1947). "The Condensation of 1,1-Diarylethylenes with Maleic Anhydride". <i><a href="/wiki/Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></i>. <b>69</b> (7): 1773–1777. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01199a055">10.1021/ja01199a055</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20251415">20251415</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=The+Condensation+of+1%2C1-Diarylethylenes+with+Maleic+Anhydride&rft.volume=69&rft.issue=7&rft.pages=1773-1777&rft.date=1947&rft_id=info%3Adoi%2F10.1021%2Fja01199a055&rft_id=info%3Apmid%2F20251415&rft.aulast=Bergmann&rft.aufirst=F.&rft.au=Szmuszkowicz%2C+J.&rft.au=Fawaz%2C+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBennettHuangMathesonSmith1982" class="citation book cs1">Bennett, M. A.; Huang, T. N.; Matheson, T. W.; Smith, A. K. (1982). <i>(η<sup>6</sup>-Hexamethylbenzene)ruthenium Complexes</i>. <a href="/wiki/Inorganic_Syntheses" title="Inorganic Syntheses">Inorganic Syntheses</a>. Vol. 21. pp. 74–78. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470132524.ch16">10.1002/9780470132524.ch16</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470132524" title="Special:BookSources/9780470132524"><bdi>9780470132524</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=%28%CE%B7%3Csup%3E6%3C%2Fsup%3E-Hexamethylbenzene%29ruthenium+Complexes&rft.series=Inorganic+Syntheses&rft.pages=74-78&rft.date=1982&rft_id=info%3Adoi%2F10.1002%2F9780470132524.ch16&rft.isbn=9780470132524&rft.aulast=Bennett&rft.aufirst=M.+A.&rft.au=Huang%2C+T.+N.&rft.au=Matheson%2C+T.+W.&rft.au=Smith%2C+A.+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShimizuWatanabeKataokaShoji2005" class="citation book cs1">Shimizu, S.; Watanabe, N.; Kataoka, T.; Shoji, T.; Abe, N.; Morishita, S.; Ichimura, H. (2005). "Pyridine and Pyridine Derivatives". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <a href="/wiki/Wiley-VCH" title="Wiley-VCH">Wiley-VCH</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a22_399">10.1002/14356007.a22_399</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3527306730" title="Special:BookSources/3527306730"><bdi>3527306730</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Pyridine+and+Pyridine+Derivatives&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pub=Wiley-VCH&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2F14356007.a22_399&rft.isbn=3527306730&rft.aulast=Shimizu&rft.aufirst=S.&rft.au=Watanabe%2C+N.&rft.au=Kataoka%2C+T.&rft.au=Shoji%2C+T.&rft.au=Abe%2C+N.&rft.au=Morishita%2C+S.&rft.au=Ichimura%2C+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHorningStrombergLloyd1952" class="citation journal cs1">Horning, E. C.; Stromberg, V. L.; Lloyd, H. A. (1952). "Beckmann Rearrangements. An Investigation of Special Cases". <i><a href="/wiki/Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></i>. <b>74</b> (20): 5153–5155. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01140a048">10.1021/ja01140a048</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Beckmann+Rearrangements.+An+Investigation+of+Special+Cases&rft.volume=74&rft.issue=20&rft.pages=5153-5155&rft.date=1952&rft_id=info%3Adoi%2F10.1021%2Fja01140a048&rft.aulast=Horning&rft.aufirst=E.+C.&rft.au=Stromberg%2C+V.+L.&rft.au=Lloyd%2C+H.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClaydenGreevesWarrenWothers2001" class="citation book cs1"><a href="/wiki/Jonathan_Clayden" title="Jonathan Clayden">Clayden, J.</a>; Greeves, N.; <a href="/wiki/Stuart_Warren" title="Stuart Warren">Warren, S.</a>; <a href="/wiki/Peter_Wothers" title="Peter Wothers">Wothers, P.</a> (2001). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00clay_0/page/531"><i>Organic Chemistry</i></a></span> (1st ed.). <a href="/wiki/Oxford_University_Press" title="Oxford University Press">Oxford University Press</a>. p. <a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00clay_0/page/531">531</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780198503460" title="Special:BookSources/9780198503460"><bdi>9780198503460</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.pages=531&rft.edition=1st&rft.pub=Oxford+University+Press&rft.date=2001&rft.isbn=9780198503460&rft.aulast=Clayden&rft.aufirst=J.&rft.au=Greeves%2C+N.&rft.au=Warren%2C+S.&rft.au=Wothers%2C+P.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Forganicchemistry00clay_0%2Fpage%2F531&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCapponiGutHellrungPersy1999" class="citation journal cs1">Capponi, M.; Gut, I. G.; Hellrung, B.; Persy, G.; Wirz, J. (1999). "Ketonization Equilibria of Phenol in Aqueous Solution". <i><a href="/wiki/Canadian_Journal_of_Chemistry" title="Canadian Journal of Chemistry">Canadian Journal of Chemistry</a></i>. <b>77</b> (5–6): 605–613. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fcjc-77-5-6-605">10.1139/cjc-77-5-6-605</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Canadian+Journal+of+Chemistry&rft.atitle=Ketonization+Equilibria+of+Phenol+in+Aqueous+Solution&rft.volume=77&rft.issue=5%E2%80%936&rft.pages=605-613&rft.date=1999&rft_id=info%3Adoi%2F10.1139%2Fcjc-77-5-6-605&rft.aulast=Capponi&rft.aufirst=M.&rft.au=Gut%2C+I.+G.&rft.au=Hellrung%2C+B.&rft.au=Persy%2C+G.&rft.au=Wirz%2C+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKündigGarciaLombergetBernardinelli2005" class="citation journal cs1">Kündig, E. P.; Garcia, A. E.; Lomberget, T.; Bernardinelli, G. (2005). "Rediscovery, Isolation, and Asymmetric Reduction of 1,2,3,4-Tetrahydronaphthalene-1,4-dione and Studies of its [Cr(CO)<sub>3</sub>] Complex". <i><a href="/wiki/Angewandte_Chemie_International_Edition" class="mw-redirect" title="Angewandte Chemie International Edition">Angewandte Chemie International Edition</a></i>. <b>45</b> (1): 98–101. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.200502588">10.1002/anie.200502588</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16304647">16304647</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition&rft.atitle=Rediscovery%2C+Isolation%2C+and+Asymmetric+Reduction+of+1%2C2%2C3%2C4-Tetrahydronaphthalene-1%2C4-dione+and+Studies+of+its+%5BCr%28CO%29%3Csub%3E3%3C%2Fsub%3E%5D+Complex&rft.volume=45&rft.issue=1&rft.pages=98-101&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2Fanie.200502588&rft_id=info%3Apmid%2F16304647&rft.aulast=K%C3%BCndig&rft.aufirst=E.+P.&rft.au=Garcia%2C+A.+E.&rft.au=Lomberget%2C+T.&rft.au=Bernardinelli%2C+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCottonWilkinson1999" class="citation book cs1"><a href="/wiki/F._Albert_Cotton" title="F. Albert Cotton">Cotton, F. A.</a>; <a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Wilkinson, G.</a> (1999). <i>Advanced Inorganic Chemistry</i> (6th ed.). <a href="/wiki/John_Wiley_and_Sons" class="mw-redirect" title="John Wiley and Sons">John Wiley and Sons</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471199571" title="Special:BookSources/9780471199571"><bdi>9780471199571</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Inorganic+Chemistry&rft.edition=6th&rft.pub=John+Wiley+and+Sons&rft.date=1999&rft.isbn=9780471199571&rft.aulast=Cotton&rft.aufirst=F.+A.&rft.au=Wilkinson%2C+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMohamedPetersonAlabugin2013" class="citation journal cs1">Mohamed, R. K.; Peterson, P. W.; Alabugin, I. V. (2013). "Concerted Reactions that Produce Diradicals and Zwitterions: Electronic, Steric, Conformational and Kinetic Control of Cycloaromatization Processes". <i><a href="/wiki/Chemical_Reviews" title="Chemical Reviews">Chemical Reviews</a></i>. <b>113</b> (9): 7089–7129. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr4000682">10.1021/cr4000682</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23600723">23600723</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=Concerted+Reactions+that+Produce+Diradicals+and+Zwitterions%3A+Electronic%2C+Steric%2C+Conformational+and+Kinetic+Control+of+Cycloaromatization+Processes&rft.volume=113&rft.issue=9&rft.pages=7089-7129&rft.date=2013&rft_id=info%3Adoi%2F10.1021%2Fcr4000682&rft_id=info%3Apmid%2F23600723&rft.aulast=Mohamed&rft.aufirst=R.+K.&rft.au=Peterson%2C+P.+W.&rft.au=Alabugin%2C+I.+V.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAromatization" class="Z3988"></span></span> </li> </ol></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Aromatization&oldid=1256231057">https://en.wikipedia.org/w/index.php?title=Aromatization&oldid=1256231057</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Hydrogen" title="Category:Hydrogen">Hydrogen</a></li><li><a href="/wiki/Category:Oil_refining" title="Category:Oil refining">Oil refining</a></li><li><a href="/wiki/Category:Organic_redox_reactions" title="Category:Organic redox reactions">Organic redox reactions</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:CS1_German-language_sources_(de)" title="Category:CS1 German-language sources (de)">CS1 German-language sources (de)</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 8 November 2024, at 22:18<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Aromatization&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/static/images/footer/wikimedia-button.svg" width="84" height="29" alt="Wikimedia Foundation" loading="lazy"></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/w/resources/assets/poweredby_mediawiki.svg" alt="Powered by MediaWiki" width="88" height="31" loading="lazy"></a></li> </ul> </footer> </div> </div> </div> <div class="vector-settings" id="p-dock-bottom"> <ul></ul> </div><script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-6b7f745dd4-9zhgt","wgBackendResponseTime":184,"wgPageParseReport":{"limitreport":{"cputime":"0.330","walltime":"0.437","ppvisitednodes":{"value":2378,"limit":1000000},"postexpandincludesize":{"value":66449,"limit":2097152},"templateargumentsize":{"value":3271,"limit":2097152},"expansiondepth":{"value":16,"limit":100},"expensivefunctioncount":{"value":1,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":65652,"limit":5000000},"entityaccesscount":{"value":0,"limit":400},"timingprofile":["100.00% 372.332 1 -total"," 62.65% 233.271 1 Template:Reflist"," 27.11% 100.942 1 Template:Short_description"," 25.56% 95.156 1 Template:March6th"," 15.22% 56.656 9 Template:Cite_book"," 13.80% 51.373 8 Template:Cite_journal"," 12.47% 46.415 3 Template:Main_other"," 11.73% 43.684 1 Template:SDcat"," 11.55% 42.995 2 Template:Pagetype"," 7.08% 26.360 6 Template:Chem"]},"scribunto":{"limitreport-timeusage":{"value":"0.200","limit":"10.000"},"limitreport-memusage":{"value":5295307,"limit":52428800}},"cachereport":{"origin":"mw-web.eqiad.main-5dc468848-r4vhn","timestamp":"20241122141544","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Aromatization","url":"https:\/\/en.wikipedia.org\/wiki\/Aromatization","sameAs":"http:\/\/www.wikidata.org\/entity\/Q698026","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q698026","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2005-07-09T09:59:07Z","dateModified":"2024-11-08T22:18:50Z","headline":"quimic reaction in which a aromatic system is formed"}</script> </body> </html>