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href="//nl.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://nl.wikipedia.org/wiki/Difenyldiselenide"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.nl"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom-feed" href="/w/index.php?title=Speciaal:RecenteWijzigingen&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-Difenyldiselenide rootpage-Difenyldiselenide skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Naar inhoud springen</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="Hoofdmenu" > <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">Hoofdmenu</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">Hoofdmenu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">naar zijbalk verplaatsen</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">verbergen</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigatie </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage" class="mw-list-item"><a href="/wiki/Hoofdpagina" title="Naar de hoofdpagina gaan [z]" accesskey="z"><span>Hoofdpagina</span></a></li><li id="n-zoekartikel" class="mw-list-item"><a href="/wiki/Portaal:Navigatie"><span>Vind een artikel</span></a></li><li id="n-today" class="mw-list-item"><a href="/wiki/18_november"><span>Vandaag</span></a></li><li id="n-Etalage" class="mw-list-item"><a href="/wiki/Wikipedia:Etalage"><span>Etalage</span></a></li><li id="n-categories" class="mw-list-item"><a href="/wiki/Categorie:Alles"><span>Categorieën</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Speciaal:RecenteWijzigingen" title="Een lijst met recente wijzigingen in deze wiki. [r]" accesskey="r"><span>Recente wijzigingen</span></a></li><li id="n-newpages" class="mw-list-item"><a href="/wiki/Speciaal:NieuwePaginas"><span>Nieuwe artikelen</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Speciaal:Willekeurig" title="Een willekeurige pagina bekijken [x]" accesskey="x"><span>Willekeurige pagina</span></a></li> </ul> </div> </div> <div id="p-navigation2" class="vector-menu mw-portlet mw-portlet-navigation2" > <div class="vector-menu-heading"> Informatie </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-portal" class="mw-list-item"><a href="/wiki/Portaal:Gebruikersportaal" title="Informatie over het project: wat u kunt doen, waar u dingen kunt vinden"><span>Gebruikersportaal</span></a></li><li id="n-Snelcursus" class="mw-list-item"><a href="/wiki/Wikipedia:Snelcursus"><span>Snelcursus</span></a></li><li id="n-help" class="mw-list-item"><a href="/wiki/Portaal:Hulp_en_beheer" title="Hulpinformatie over deze wiki"><span>Hulp en contact</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Hoofdpagina" 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="de vrije encyclopedie" src="/static/images/mobile/copyright/wikipedia-tagline-nl.svg" width="120" height="13" style="width: 7.5em; 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/Speciaal:Zoeken" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Doorzoek Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Zoeken</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="Doorzoek Wikipedia" aria-label="Doorzoek Wikipedia" autocapitalize="sentences" title="Doorzoek 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="Speciaal:Zoeken"> </div> <button class="cdx-button cdx-search-input__end-button">Zoeken</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Persoonlijke hulpmiddelen"> <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="Uiterlijk"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="De lettergrootte, breedte en kleur van de pagina wijzigen" > <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="Uiterlijk" > <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">Uiterlijk</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="//donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_nl.wikipedia.org&uselang=nl" class=""><span>Doneren</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=Speciaal:GebruikerAanmaken&returnto=Difenyldiselenide" title="Registreer u vooral en meld u aan. Dit is echter niet verplicht." class=""><span>Account aanmaken</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=Speciaal:Aanmelden&returnto=Difenyldiselenide" title="U wordt van harte uitgenodigd om aan te melden, maar dit is niet verplicht [o]" accesskey="o" class=""><span>Aanmelden</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="Meer opties" > <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="Persoonlijke hulpmiddelen" > <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">Persoonlijke hulpmiddelen</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="Gebruikersmenu" > <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="//donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_nl.wikipedia.org&uselang=nl"><span>Doneren</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Speciaal:GebruikerAanmaken&returnto=Difenyldiselenide" title="Registreer u vooral en meld u aan. Dit is echter niet verplicht."><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Account aanmaken</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Speciaal:Aanmelden&returnto=Difenyldiselenide" title="U wordt van harte uitgenodigd om aan te melden, maar dit is niet verplicht [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Aanmelden</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"> Pagina's voor uitgelogde redacteuren <a href="/wiki/Help:Inleiding" aria-label="Meer leren over bewerken"><span>meer lezen</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/Speciaal:MijnBijdragen" title="Bijdragen IP-adres [y]" accesskey="y"><span>Bijdragen</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Speciaal:MijnOverleg" title="Overlegpagina van de anonieme gebruiker van dit IP-adres [n]" accesskey="n"><span>Overleg</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="Inhoud" 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">Inhoud</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">naar zijbalk verplaatsen</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">verbergen</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-Synthese" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthese"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Synthese</span> </div> </a> <ul id="toc-Synthese-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reacties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reacties"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Reacties</span> </div> </a> <ul id="toc-Reacties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Externe_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Externe_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Externe links</span> </div> </a> <ul id="toc-Externe_links-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="Inhoud" 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="Inhoudsopgave omschakelen" > <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">Inhoudsopgave omschakelen</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">Difenyldiselenide</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="Ga naar een artikel in een andere taal. Beschikbaar in 11 talen" > <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-11" 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">11 talen</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%AB%D9%86%D8%A7%D8%A6%D9%8A_%D8%B3%D9%8A%D9%84%D9%8A%D9%86%D9%8A%D8%AF_%D8%AB%D9%86%D8%A7%D8%A6%D9%8A_%D8%A7%D9%84%D9%81%D9%8A%D9%86%D9%8A%D9%84" title="ثنائي سيلينيد ثنائي الفينيل – Arabisch" lang="ar" hreflang="ar" data-title="ثنائي سيلينيد ثنائي الفينيل" data-language-autonym="العربية" data-language-local-name="Arabisch" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AF%DB%8C%E2%80%8C%D9%81%D9%86%DB%8C%D9%84_%D8%AF%DB%8C%E2%80%8C%D8%B3%D9%84%D9%86%DB%8C%D8%AF" title="دی‌فنیل دی‌سلنید – South Azerbaijani" lang="azb" hreflang="azb" data-title="دی‌فنیل دی‌سلنید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Difenyldiselenid" title="Difenyldiselenid – Tsjechisch" lang="cs" hreflang="cs" data-title="Difenyldiselenid" data-language-autonym="Čeština" data-language-local-name="Tsjechisch" 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/Diphenyldiselenid" title="Diphenyldiselenid – Duits" lang="de" hreflang="de" data-title="Diphenyldiselenid" data-language-autonym="Deutsch" data-language-local-name="Duits" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Diphenyl_diselenide" title="Diphenyl diselenide – Engels" lang="en" hreflang="en" data-title="Diphenyl diselenide" data-language-autonym="English" data-language-local-name="Engels" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AF%DB%8C%E2%80%8C%D9%81%D9%86%DB%8C%D9%84_%D8%AF%DB%8C%E2%80%8C%D8%B3%D9%84%D9%86%DB%8C%D8%AF" title="دی‌فنیل دی‌سلنید – Perzisch" lang="fa" hreflang="fa" data-title="دی‌فنیل دی‌سلنید" data-language-autonym="فارسی" data-language-local-name="Perzisch" 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/Dis%C3%A9l%C3%A9niure_de_diph%C3%A9nyle" title="Diséléniure de diphényle – Frans" lang="fr" hreflang="fr" data-title="Diséléniure de diphényle" data-language-autonym="Français" data-language-local-name="Frans" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Disseleneto_de_difenila" title="Disseleneto de difenila – Portugees" lang="pt" hreflang="pt" data-title="Disseleneto de difenila" data-language-autonym="Português" data-language-local-name="Portugees" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Difenil_diselenid" title="Difenil diselenid – Servo-Kroatisch" lang="sh" hreflang="sh" data-title="Difenil diselenid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Servo-Kroatisch" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Difenil_diselenid" title="Difenil diselenid – Servisch" lang="sr" hreflang="sr" data-title="Difenil diselenid" data-language-autonym="Српски / srpski" data-language-local-name="Servisch" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E4%BA%8C%E7%A1%92%E9%86%9A" title="二苯基二硒醚 – Chinees" lang="zh" hreflang="zh" data-title="二苯基二硒醚" data-language-autonym="中文" data-language-local-name="Chinees" class="interlanguage-link-target"><span>中文</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/Q3538196#sitelinks-wikipedia" title="Taalkoppelingen 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lang="nl" dir="ltr"><table class="infobox" cellpadding="1" cellspacing="1"> <tbody><tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center; font-size:120%;" colspan="3">Difenyldiselenide </th></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center;" colspan="3">Structuurformule en molecuulmodel </th></tr> <tr> <td style="text-align:center; padding:0;" colspan="3"><span typeof="mw:File"><a href="/wiki/Bestand:Diphenyl_diselenide.png" class="mw-file-description"><img alt="Structuurformule van difenyldiselenide" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Diphenyl_diselenide.png/175px-Diphenyl_diselenide.png" decoding="async" width="175" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Diphenyl_diselenide.png/263px-Diphenyl_diselenide.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Diphenyl_diselenide.png/350px-Diphenyl_diselenide.png 2x" data-file-width="1876" data-file-height="1065" /></a></span> </td></tr> <tr> <td style="text-align:center;" colspan="3"><div style="font-size:90%"><a href="/wiki/Structuurformule" title="Structuurformule">Structuurformule</a> van difenyldiselenide</div> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center;" colspan="3">Algemeen </th></tr> <tr> <th><a href="/wiki/Molecuulformule" title="Molecuulformule">Molecuulformule</a> </th> <td colspan="2">C<sub>12</sub>H<sub>10</sub>Se<sub>2</sub> </td></tr> <tr> <th><a href="/wiki/IUPAC-nomenclatuur" title="IUPAC-nomenclatuur">IUPAC-naam</a> </th> <td colspan="2">difenyldiselenide </td></tr> <tr> <th><a href="/wiki/Molaire_massa" title="Molaire massa">Molmassa</a> </th> <td colspan="2">312,13 <a href="/wiki/Gram_(eenheid)" title="Gram (eenheid)">g</a>/<a href="/wiki/Mol_(eenheid)" title="Mol (eenheid)">mol</a> </td></tr> <tr> <th><a href="/wiki/SMILES" title="SMILES">SMILES</a> </th> <td colspan="2"><div style="word-wrap:break-word; width:127px;">c1ccc(cc1)[Se][Se]c2ccccc2</div> </td></tr> <tr> <th><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a> </th> <td colspan="2"><div style="word-wrap:break-word; width:127px;">1/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H</div> </td></tr> <tr> <th><a href="/wiki/CAS-nummer" title="CAS-nummer">CAS-nummer</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1666-13-3">1666-13-3</a> </td></tr> <tr> <th><a href="/wiki/PubChem" title="PubChem">PubChem</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=15460">15460</a> </td></tr> <tr> <th><a href="/wiki/Wikidata" title="Wikidata">Wikidata</a> </th> <td colspan="2"><a href="https://www.wikidata.org/wiki/Q3538196" class="extiw" title="d:Q3538196">Q3538196</a> </td></tr> <tr> <th>Beschrijving </th> <td colspan="2">Oranje poeder </td></tr> <tr> <th>Vergelijkbaar met </th> <td colspan="2"><a href="/wiki/Benzeenselenol" title="Benzeenselenol">benzeenselenol</a><br /><a href="/wiki/Difenyldisulfide" title="Difenyldisulfide">difenyldisulfide</a> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3">Waarschuwingen en veiligheidsmaatregelen </th></tr> <tr> <td class="ta-center" colspan="3"><table align="center" style="border-style:none;"><tbody><tr><td style="margin-left:auto;margin-right:auto;vertical-align:top;text-align:center;border-style:none;cell-padding:2px"><span typeof="mw:File"><a href="/wiki/Bestand:GHS-pictogram-skull.svg" class="mw-file-description" title="Toxisch"><img alt="Toxisch" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/60px-GHS-pictogram-skull.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/90px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/120px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span></td><td style="margin-left:auto;margin-right:auto;vertical-align:top;text-align:center;border-style:none;cell-padding:2px"><span typeof="mw:File"><a href="/wiki/Bestand:GHS-pictogram-silhouette.svg" class="mw-file-description" title="Schadelijk voor de gezondheid"><img alt="Schadelijk voor de gezondheid" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/60px-GHS-pictogram-silhouette.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/90px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/120px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span></td><td style="margin-left:auto;margin-right:auto;vertical-align:top;text-align:center;border-style:none;cell-padding:2px"><span typeof="mw:File"><a href="/wiki/Bestand:GHS-pictogram-pollu.svg" class="mw-file-description" title="Milieugevaarlijk"><img alt="Milieugevaarlijk" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/60px-GHS-pictogram-pollu.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/90px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/120px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span></td></tr></tbody></table><b>Gevaar</b> </td></tr> <tr> <th><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">H-zinnen</a> </th> <td colspan="2"><abbr title="Giftig bij inslikken.">H301</abbr> - <abbr title="Giftig bij inademing.">H331</abbr> - <abbr title="Kan schade aan organen ''<of alle betrokken organen vermelden indien bekend>'' veroorzaken bij langdurige of herhaalde blootstelling ''<blootstellingsroute vermelden indien afdoende bewezen is dat het gevaar bij andere blootstellingsroutes niet aanwezig is>''.">H373</abbr> - <abbr title="Zeer giftig voor in het water levende organismen, met langdurige gevolgen.">H410</abbr> </td></tr> <tr> <th><span class="nowrap"><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">EUH-zinnen</a></span> </th> <td colspan="2"><i>geen</i> </td></tr> <tr> <th><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">P-zinnen</a> </th> <td colspan="2"><abbr title="Inademing van stof/rook/gas/nevel/damp/spuitnevel vermijden.">P261</abbr> - <abbr title="Voorkom lozing in het milieu.">P273</abbr> - <abbr title="Na inslikken: onmiddellijk een antigifcentrum of een arts raadplegen.">P301+P310</abbr> - <abbr title="Een antigifcentrum of een arts raadplegen.">P311</abbr> - <abbr title="Inhoud/verpakking afvoeren naar ...">P501</abbr> </td></tr> <tr> <th><a href="/wiki/Stofidentificatienummer" title="Stofidentificatienummer">VN-nummer</a> </th> <td colspan="2">3283 </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3">Fysische eigenschappen </th></tr> <tr> <th><a href="/wiki/Aggregatietoestand" title="Aggregatietoestand">Aggregatietoestand</a> </th> <td colspan="2">vast </td></tr> <tr> <th><a href="/wiki/Kleur_(hoofdbetekenis)" class="mw-redirect" title="Kleur (hoofdbetekenis)">Kleur</a> </th> <td colspan="2">oranje </td></tr> <tr> <th><a href="/wiki/Massadichtheid" title="Massadichtheid">Dichtheid</a> </th> <td colspan="2">1,84 g/cm³ </td></tr> <tr> <th><a href="/wiki/Smeltpunt" title="Smeltpunt">Smeltpunt</a> </th> <td colspan="2">59 - 61 °C </td></tr> <tr> <th><a href="/wiki/Oplosbaarheid" title="Oplosbaarheid">Oplosbaarheid</a> in <a href="/wiki/Water" title="Water">water</a> </th> <td colspan="2">niet g/L </td></tr> <tr> <th>Goed oplosbaar in </th> <td colspan="2">dichloormethaan </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3">Geometrie en kristalstructuur </th></tr> <tr> <th><a href="/wiki/Dipoolmoment" title="Dipoolmoment">Dipoolmoment</a> </th> <td colspan="2">0 <a href="/wiki/Debye_(eenheid)" title="Debye (eenheid)">D</a> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3"><small>Tenzij anders vermeld zijn <a href="/wiki/Standaardomstandigheden" title="Standaardomstandigheden">standaardomstandigheden</a> gebruikt (298,15 <a href="/wiki/Kelvin_(eenheid)" title="Kelvin (eenheid)">K</a> of 25 <a href="/wiki/Celsius" title="Celsius">°C</a>, 1 <a href="/wiki/Bar_(druk)" title="Bar (druk)">bar</a>).</small> </th></tr> <tr> <td class="infobox-kop notheme center" style="background-color:#DDEEFF; color:inherit;" colspan="3"> <table cellspacing="0" cellpadding="0"> <tbody><tr> <td style="vertical-align:middle;"><b>Portaal</b>  <span class="noviewer" typeof="mw:File"><a href="/wiki/Bestand:Portal.svg" class="mw-file-description" title="Portaalicoon"><img alt="Portaalicoon" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/22px-Portal.svg.png" decoding="async" width="22" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/33px-Portal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/44px-Portal.svg.png 2x" data-file-width="36" data-file-height="32" /></a></span>   </td> <td class="ta-left"><b><a href="/wiki/Portaal:Scheikunde" title="Portaal:Scheikunde">Scheikunde</a> </b> </td></tr></tbody></table> </td></tr> </tbody></table> <p><b>Difenyldiselenide</b> is een <a href="/wiki/Organoseleenchemie" title="Organoseleenchemie">organoseleenverbinding</a> met als <a href="/wiki/Brutoformule" title="Brutoformule">brutoformule</a> C<sub>12</sub>H<sub>10</sub>Se<sub>2</sub>. De formule wordt vaak afgekort tot Ph<sub>2</sub>Se<sub>2</sub>. Deze oranje <a href="/wiki/Vaste_stof" title="Vaste stof">vaste stof</a> is het eerste oxidatieproduct van <a href="/wiki/Benzeenselenol" title="Benzeenselenol">benzeenselenol</a>. In de <a href="/wiki/Organische_synthese" title="Organische synthese">organische synthese</a> wordt de stof gebruikt als bron voor de fenylselenide-eenheid. De centrale Se-Se-binding heeft een lengte van 229 <a href="/wiki/Picometer" title="Picometer">pm</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthese">Synthese</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Difenyldiselenide&veaction=edit&section=1" title="Bewerk dit kopje: Synthese" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Difenyldiselenide&action=edit&section=1" title="De broncode bewerken van de sectie: Synthese"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Difenyldiselenide wordt bereid in een tweestapssynthese via <a href="/wiki/Oxidatie" title="Oxidatie">oxidatie</a> van het benzeenselenolaat, dat zelf bereid wordt uit <a href="/wiki/Fenylmagnesiumbromide" title="Fenylmagnesiumbromide">fenylmagnesiumbromide</a>:<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {C6H5MgBr + Se -> C6H5SeMgBr}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>MgBr</mtext> <mo>+</mo> <mtext>Se</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>SeMgBr</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {C6H5MgBr + Se -> C6H5SeMgBr}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/2fcb2300f138dade95e7af6b01cfac7057a11a7f" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:35.347ex; height:2.843ex;" alt="{\displaystyle {\ce {C6H5MgBr + Se -> C6H5SeMgBr}}}"></span></dd> <dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2C6H5SeMgBr + Br2 -> (C6H5)2Se2 + 2MgBr2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>SeMgBr</mtext> <mo>+</mo> <msubsup> <mtext>Br</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>Se</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>MgBr</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2C6H5SeMgBr + Br2 -> (C6H5)2Se2 + 2MgBr2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/8ba24746bc3cbbbfc5a7070c1252ac263701e4be" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:49.87ex; height:3.009ex;" alt="{\displaystyle {\ce {2C6H5SeMgBr + Br2 -> (C6H5)2Se2 + 2MgBr2}}}"></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Reacties">Reacties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Difenyldiselenide&veaction=edit&section=2" title="Bewerk dit kopje: Reacties" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Difenyldiselenide&action=edit&section=2" title="De broncode bewerken van de sectie: Reacties"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>De <a href="/wiki/Reductie_(scheikunde)" title="Reductie (scheikunde)">reductie</a> met <a href="/wiki/Natrium" title="Natrium">natrium</a> levert natriumfenylselenolaat: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(C6H5)2Se2 + 2Na -> 2C6H5SeNa}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>Se</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>Na</mtext> <mo stretchy="false">⟶</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>SeNa</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(C6H5)2Se2 + 2Na -> 2C6H5SeNa}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/ae080c55132e34ec8c0a126ef091e6c873b82eb6" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:36.473ex; height:3.009ex;" alt="{\displaystyle {\ce {(C6H5)2Se2 + 2Na -> 2C6H5SeNa}}}"></span></dd></dl> <p>Natriumfenylselenolaat is een goed bruikbaar <a href="/wiki/Nucleofiel" title="Nucleofiel">nucleofiel</a>: het <a href="/wiki/Elektronegativiteit" title="Elektronegativiteit">elektropositieve</a> natrium genereert een negatieve lading op seleen. De fenylselenylgroep kan via een <a href="/wiki/Nucleofiele_substitutie" title="Nucleofiele substitutie">nucleofiele substitutie</a> van <a href="/wiki/Halogeenalkaan" title="Halogeenalkaan">alkylhalogeniden</a>, <a href="/wiki/Sulfonaat" class="mw-redirect" title="Sulfonaat">alkylsulfonaten</a>, (<a href="/wiki/Mesylaat" class="mw-redirect" title="Mesylaat">mesylaten</a> of <a href="/wiki/Tosylaat" class="mw-redirect" title="Tosylaat">tosylaten</a>) of <a href="/wiki/Epoxide" title="Epoxide">epoxiden</a> in een organische verbinding gebracht worden. Onderstaand voorbeeld is ontleend aan de synthese van <a href="/wiki/Morfine" title="Morfine">morfine</a>.<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> </p> <dl><dd><figure class="mw-halign-left" typeof="mw:File"><a href="/wiki/Bestand:NaSePh-Epoxide1.svg" class="mw-file-description" title="Opening van een epoxide met natriumfenylselenolaat"><img alt="Opening van een epoxide met natriumfenylselenolaat" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/NaSePh-Epoxide1.svg/600px-NaSePh-Epoxide1.svg.png" decoding="async" width="600" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/NaSePh-Epoxide1.svg/900px-NaSePh-Epoxide1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/NaSePh-Epoxide1.svg/1200px-NaSePh-Epoxide1.svg.png 2x" data-file-width="512" data-file-height="89" /></a><figcaption>Opening van een epoxide met natriumfenylselenolaat</figcaption></figure></dd></dl> <div style="clear:left;"></div> <p>De reactie met <a href="/wiki/Dichloor" title="Dichloor">dichloor</a> levert fenylselenylchloride, een <a href="/wiki/Elektrofiel" title="Elektrofiel">elektrofiel</a>: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(C6H5)2Se2 + Cl2 -> 2C6H5SeCl}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>Se</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>Cl</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>SeCl</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(C6H5)2Se2 + Cl2 -> 2C6H5SeCl}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/7c05522b1f1eaa068ae3fea3c0609fe4a19c6cc9" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:34.817ex; height:3.009ex;" alt="{\displaystyle {\ce {(C6H5)2Se2 + Cl2 -> 2C6H5SeCl}}}"></span></dd></dl> <p>Door de reactie met een nucleofiel kan de fenylselenylgropep in een organische verbinding worden geïntroduceerd. Als nucleofielen kunnen <a href="/wiki/Enolaat" title="Enolaat">enolaten</a>, <a href="/wiki/Silylether" title="Silylether">enolsilylethers</a>, <a href="/wiki/Grignard-reagens" title="Grignard-reagens">Grignard-reagentia</a>, <a href="/wiki/Organolithiumchemie" title="Organolithiumchemie">organolithiumverbindingen</a>, <a href="/wiki/Alkeen" title="Alkeen">alkenen</a> en <a href="/wiki/Amine" title="Amine">amines</a> optreden. In het voorbeeld hieronder, de eerste stappen in de synthese van <a href="/w/index.php?title=Strychnofoline&action=edit&redlink=1" class="new" title="Strychnofoline (de pagina bestaat niet)">strychnofoline</a>, wordt een fenylselenylgroep geïntroduceerd via het enolaat van een <a href="/wiki/Lactam" title="Lactam">lactam</a>:<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> <dl><dd><figure class="mw-halign-left" typeof="mw:File"><a href="/wiki/Bestand:ClSePh-enone1.svg" class="mw-file-description" title="Omzetting van een carbonylverbinding naar een α,β-onverzadigde analoog"><img alt="Omzetting van een carbonylverbinding naar een α,β-onverzadigde analoog" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/ClSePh-enone1.svg/600px-ClSePh-enone1.svg.png" decoding="async" width="600" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/ClSePh-enone1.svg/900px-ClSePh-enone1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6a/ClSePh-enone1.svg/1200px-ClSePh-enone1.svg.png 2x" data-file-width="512" data-file-height="72" /></a><figcaption>Omzetting van een carbonylverbinding naar een α,β-onverzadigde analoog</figcaption></figure></dd></dl> <div style="clear:left;"></div> <p>Deze methode is een belangrijk stuk organisch-synthetisch gereedschap voor de omzetting van <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonylverbindingen</a> naar hun <a href="/wiki/Alfa,b%C3%A8ta-onverzadigde_carbonylverbinding" title="Alfa,bèta-onverzadigde carbonylverbinding">α,β-onverzadigde analoga</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> </p><p>Met krachtige nucleofielen kan difenyldiselenide zelf als elektrofiel optreden, het nucleofiel is dan een Grignard- of organolithium-reagens of het enolaat van een ester. Enolaten van ketonen reageren niet. Meestal wordt de voorkeur gegeven aan fenylselenylchloride, omdat bij de reactie met difenyldiselenide de helft van het selenidereagens als <a href="/wiki/Leaving_group" title="Leaving group">leaving group</a> optreedt, en dus eigenlijk verspild wordt: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(C6H5)2Se2 + Nu- -> C6H5SeNu + C6H5Se-}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>Se</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msup> <mtext>Nu</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>SeNu</mtext> <mo>+</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msup> <mtext>Se</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(C6H5)2Se2 + Nu- -> C6H5SeNu + C6H5Se-}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/dfeaf0880a543000ae89968106ce9e7283fe5d4c" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:47.351ex; height:3.176ex;" alt="{\displaystyle {\ce {(C6H5)2Se2 + Nu- -> C6H5SeNu + C6H5Se-}}}"></span></dd></dl> <p>N-fenylselenoftaalimide (N-PSP) kan gebruikt worden als fenylselenylchloride een te sterk elektrofiel is en anderzijds difenyldiselenide niet <a href="/wiki/Reactiviteit_(scheikunde)" title="Reactiviteit (scheikunde)">reactief</a> genoeg of te duur is.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Externe_links">Externe links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Difenyldiselenide&veaction=edit&section=3" title="Bewerk dit kopje: Externe links" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Difenyldiselenide&action=edit&section=3" title="De broncode bewerken van de sectie: Externe links"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><style data-mw-deduplicate="TemplateStyles:r67679320">.mw-parser-output .taalaanduiding{font-family:sans-serif;font-size:85%;cursor:help;color:var(--color-subtle,#555)}.mw-parser-output .taalaanduiding span{border-bottom:1px dotted var(--color-subtle,#555)}</style><span class="taalaanduiding" title="Taal: Engels">(<span>en</span>) </span> <a rel="nofollow" class="external text" href="http://fscimage.fishersci.com/msds/44783.htm">MSDS van <i>difenyldiselenide</i></a></li></ul> <div class="toccolours appendix" role="presentation" style="font-size:90%; margin:1em 0 -0.5em; clear:both;"> <div><span style="font-weight:bold">Bronnen, noten en/of referenties</span></div> <div class="reflist" style="list-style-type: decimal;"><div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text"><span style="font-variant:small-caps">R.E. Marsh</span>.  (1952). <i>The Crystal Structure of Diphenyl Diselenide</i> <i><a href="/wiki/Acta_Crystallographica" title="Acta Crystallographica">Acta Crystallographica</a></i>.  <b>5</b> <span class="nowrap">pag.: 458–462</span> <span class="nowrap"><a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1107%2FS0365110X52001349">10.1107/S0365110X52001349 </a></span>  </span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text"><span style="font-variant:small-caps">H.J. Reich, M.L. Cohen, P.S. Clark</span>.  (1979). <i>Reagents for Synthesis of Organoselenium Compounds: Diphenyl Diselenide and Benzeneselenenyl Chloride</i> <i>Org Synth</i>.  <b>59</b> <span class="nowrap">pag.: 141</span> </span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><span style="font-variant:small-caps">D.F. Taber, T.B. Neubert, A.L. Rheingold</span>.  (2002). GEEN TITEL OPGEGEVEN <i>J. Amer. Chem. Soc.</i>.  <b>124</b> <span class="nowrap">pag.: 12416</span> </span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text"><span style="font-variant:small-caps">A. Lerchner, E.M. Carreira, E. M.</span>.  (2002). GEEN TITEL OPGEGEVEN <i>J. Amer. Chem. Soc.</i>. <span class="nowrap">pag.: 14826</span> </span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text"><span style="font-variant:small-caps">H.J. Reich, S. Wollowitz</span>.  (1993). <i>Preparation of α,β-Unsaturated Carbonyl Compounds and Nitriles by Selenoxide Elimination.</i> <i>Org. Reactions</i>.  <b>44</b> <span class="nowrap">pag.: 1</span> </span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text"><span style="font-variant:small-caps">Alejandro F. Barrero, E.J. Alvarez-Manzaneda, R. Chahboun, M. Corttés, V. Armstrong</span>. <i>Synthesis and antitumor activity of puupehedione and related compounds</i> <i>Tetrahedron</i>.  <b>55</b> (52):  <span class="nowrap">pag.: 15181</span> <span class="nowrap"><a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1016%2FS0040-4020%2899%2900992-8">10.1016/S0040-4020(99)00992-8 </a></span>  </span> </li> </ol></div></div> </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="">Overgenomen van "<a dir="ltr" href="https://nl.wikipedia.org/w/index.php?title=Difenyldiselenide&oldid=60227921">https://nl.wikipedia.org/w/index.php?title=Difenyldiselenide&oldid=60227921</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Categorie:Alles" title="Categorie:Alles">Categorieën</a>: <ul><li><a href="/wiki/Categorie:Organische_seleenverbinding" title="Categorie:Organische seleenverbinding">Organische seleenverbinding</a></li><li><a href="/wiki/Categorie:Toxische_stof" title="Categorie:Toxische stof">Toxische stof</a></li><li><a href="/wiki/Categorie:Milieugevaarlijke_stof" title="Categorie:Milieugevaarlijke stof">Milieugevaarlijke stof</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Verborgen categorie: <ul><li><a href="/wiki/Categorie:Wikipedia:GHS_aanwezig" title="Categorie:Wikipedia:GHS aanwezig">Wikipedia:GHS aanwezig</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"> Deze pagina is voor het laatst bewerkt op 25 okt 2021 om 11:51.</li> <li id="footer-info-copyright">De tekst is beschikbaar onder de licentie <a rel="nofollow" class="external text" href="//creativecommons.org/licenses/by-sa/4.0/deed.nl">Creative Commons Naamsvermelding/Gelijk delen</a>, er kunnen aanvullende voorwaarden van toepassing zijn. 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