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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="Vai a una voce in un'altra lingua. Disponibile in 19 lingue" > <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-19" 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">19 lingue</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%8A%D8%A7%D9%84" title="ثيال - arabo" lang="ar" hreflang="ar" data-title="ثيال" data-language-autonym="العربية" data-language-local-name="arabo" 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/Thialy" title="Thialy - ceco" lang="cs" hreflang="cs" data-title="Thialy" data-language-autonym="Čeština" data-language-local-name="ceco" 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/Thioaldehyde" title="Thioaldehyde - tedesco" lang="de" hreflang="de" data-title="Thioaldehyde" data-language-autonym="Deutsch" data-language-local-name="tedesco" 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/Thial" title="Thial - inglese" lang="en" hreflang="en" data-title="Thial" data-language-autonym="English" data-language-local-name="inglese" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Tial" title="Tial - spagnolo" lang="es" hreflang="es" data-title="Tial" data-language-autonym="Español" data-language-local-name="spagnolo" 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%AA%DB%8C%D8%A7%D9%84" title="تیال - persiano" lang="fa" hreflang="fa" data-title="تیال" data-language-autonym="فارسی" data-language-local-name="persiano" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Tioaldehydit" title="Tioaldehydit - finlandese" lang="fi" hreflang="fi" data-title="Tioaldehydit" data-language-autonym="Suomi" data-language-local-name="finlandese" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Thioald%C3%A9hyde" title="Thioaldéhyde - francese" lang="fr" hreflang="fr" data-title="Thioaldéhyde" data-language-autonym="Français" data-language-local-name="francese" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Tioaldehidek" title="Tioaldehidek - ungherese" lang="hu" hreflang="hu" data-title="Tioaldehidek" data-language-autonym="Magyar" data-language-local-name="ungherese" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%81%E3%82%A2%E3%83%BC%E3%83%AB" title="チアール - giapponese" lang="ja" hreflang="ja" data-title="チアール" data-language-autonym="日本語" data-language-local-name="giapponese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Thial" title="Thial - olandese" lang="nl" hreflang="nl" data-title="Thial" data-language-autonym="Nederlands" data-language-local-name="olandese" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Tial" title="Tial - rumeno" lang="ro" hreflang="ro" data-title="Tial" data-language-autonym="Română" data-language-local-name="rumeno" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D0%B8%D0%BE%D0%B0%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4%D1%8B" title="Тиоальдегиды - russo" lang="ru" hreflang="ru" data-title="Тиоальдегиды" data-language-autonym="Русский" data-language-local-name="russo" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Thial" title="Thial - Simple English" lang="en-simple" hreflang="en-simple" data-title="Thial" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Tioaldehyd" title="Tioaldehyd - slovacco" lang="sk" hreflang="sk" data-title="Tioaldehyd" data-language-autonym="Slovenčina" data-language-local-name="slovacco" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Tioaldehyd" title="Tioaldehyd - svedese" lang="sv" hreflang="sv" data-title="Tioaldehyd" data-language-autonym="Svenska" data-language-local-name="svedese" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%A4%E0%AF%88%E0%AE%AF%E0%AE%BE%E0%AE%B2%E0%AF%8D" title="தையால் - tamil" lang="ta" hreflang="ta" data-title="தையால்" data-language-autonym="தமிழ்" data-language-local-name="tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A2%D1%96%D0%BE%D0%B0%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D1%96%D0%B4%D0%B8" title="Тіоальдегіди - ucraino" lang="uk" hreflang="uk" data-title="Тіоальдегіди" data-language-autonym="Українська" data-language-local-name="ucraino" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A1%AB%E9%86%9B" title="硫醛 - cinese" lang="zh" hreflang="zh" data-title="硫醛" data-language-autonym="中文" data-language-local-name="cinese" 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/Q1088212#sitelinks-wikipedia" title="Modifica collegamenti 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ultime modifiche alle pagine collegate a questa [k]" accesskey="k"><span>Modifiche correlate</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Speciale:PagineSpeciali" title="Elenco di tutte le pagine speciali [q]" accesskey="q"><span>Pagine speciali</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Tioaldeidi&oldid=135340057" title="Collegamento permanente a questa versione di questa pagina"><span>Link permanente</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Tioaldeidi&action=info" title="Ulteriori informazioni su questa pagina"><span>Informazioni pagina</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Speciale:Cita&page=Tioaldeidi&id=135340057&wpFormIdentifier=titleform" title="Informazioni su come citare questa pagina"><span>Cita questa voce</span></a></li><li id="t-urlshortener" class="mw-list-item"><a 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</div> </nav> <nav class="vector-appearance-landmark" aria-label="Aspetto"> <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">Aspetto</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">sposta nella barra laterale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">nascondi</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">Da Wikipedia, l'enciclopedia libera.</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="it" dir="ltr"><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:FunktionelleGruppen_Thioaldehyde.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/FunktionelleGruppen_Thioaldehyde.svg/220px-FunktionelleGruppen_Thioaldehyde.svg.png" decoding="async" width="220" height="205" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/FunktionelleGruppen_Thioaldehyde.svg/330px-FunktionelleGruppen_Thioaldehyde.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/FunktionelleGruppen_Thioaldehyde.svg/440px-FunktionelleGruppen_Thioaldehyde.svg.png 2x" data-file-width="114" data-file-height="106" /></a><figcaption>Struttura generale delle tioaldeidi con in <span style="color:blue;"><b>blu</b></span> il gruppo funzionale tiocarbonile.</figcaption></figure> <p>Le <b>tioaldeidi</b> sono <a href="/w/index.php?title=Composto_organosolforico&action=edit&redlink=1" class="new" title="Composto organosolforico (la pagina non esiste)">composti organosolforici</a> (o zolforganici), cioè <a href="/wiki/Composto_organico" title="Composto organico">composti organici</a> contenente <a href="/wiki/Legame_chimico" title="Legame chimico">legami</a> <a href="/wiki/Carbonio" title="Carbonio">carbonio</a>-<a href="/wiki/Zolfo" title="Zolfo">zolfo</a>, aventi formula bruta C<sub>n</sub>H<sub>2n</sub>S, che recano nella loro struttura il <a href="/wiki/Gruppo_funzionale" title="Gruppo funzionale">gruppo funzionale</a> <a href="/w/index.php?title=Tioformile&action=edit&redlink=1" class="new" title="Tioformile (la pagina non esiste)">tioformile</a>, indicato con -CHS. Le tioaldeidi sono paragonabili ad <a href="/wiki/Aldeidi" title="Aldeidi">aldeidi</a>, RC(O) H, in cui un atomo di <a href="/wiki/Zolfo" title="Zolfo">zolfo</a> (S) ha sostituito l'atomo di ossigeno (O) nel doppio legame con il carbonio. </p><p>Il gruppo -C=S-H viene detto genericamente tiocarbonile o tiocarbonilico. Nelle tioaldeidi esso è legato a un atomo di idrogeno e ad un radicale <a href="/wiki/Gruppo_alchilico" class="mw-redirect" title="Gruppo alchilico">alchilico</a> o <a href="/wiki/Gruppo_arilico" class="mw-redirect" title="Gruppo arilico">arilico</a>; nella <a href="/wiki/Tioformaldeide" title="Tioformaldeide">tioformaldeide</a>, la tioaldeide più semplice, esso è legato a due atomi di idrogeno.<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><p>A causa della poca stabilità del legame carbonio zolfo rispetto a quella del legame carbonilico, le tioaldeidi sono però molto più reattive delle aldeidi, non solo, esse sono anche più reattive dei relativi <a href="/wiki/Tiochetoni" title="Tiochetoni">tiochetoni</a>, a causa del fatto che la protezione sterica di cui godono è quella data da un solo <a href="/wiki/Gruppo_sostituente" class="mw-redirect" title="Gruppo sostituente">gruppo sostituente</a>. Per questo motivo generalmente le tioaldeidi non possono essere isolate in <a href="/wiki/Condizioni_standard" title="Condizioni standard">condizioni standard</a> dato che tendono subito a polimerizzare; la già citata tioformaldeide (H<sub>2</sub>C=S), ad esempio, condensa formando il suo trimero ciclico chiamato <a href="/wiki/1,3,5-tritiano" title="1,3,5-tritiano">1,3,5-tritiano</a>, mentre la tioacroleina (H<sub>2</sub>C=CHCH=S), formata dalla decomposizione dell'<a href="/wiki/Allicina" title="Allicina">allicina</a> presente nell'<a href="/wiki/Aglio" class="mw-redirect" title="Aglio">aglio</a>, dimerizza attraverso una <a href="/wiki/Reazione_di_Diels-Alder" title="Reazione di Diels-Alder">reazione di Diels-Alder</a>, portando alla creazione di due <a href="/wiki/Vinilditiini" title="Vinilditiini">vinilditiini</a> isomeri.<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><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><p>Nonostante la sua alta instabilità alle condizioni stardard terrestri, la tioformaldeide è invece stabile in condizioni decisamente più estreme, tanto che, grazie a tecniche di <a href="/wiki/Spettroscopia_infrarossa" title="Spettroscopia infrarossa">spettroscopia infrarossa</a>, la sua presenza è stata riscontrata, assieme a quelle dei suoi <a href="/wiki/Isotopologhi" title="Isotopologhi">isotopologhi</a> mono- e di-deuterato, nelle <a href="/wiki/Nube_interstellare" title="Nube interstellare">nubi interstellari</a>, come la <a href="/wiki/Regione_H_I#Nubi_ad_alta_velocità" title="Regione H I">nube di gas ad alta velocità</a> chiamata <a href="/wiki/CO-0.40-0.22" title="CO-0.40-0.22">CO-0.40-0.22</a>.<sup id="cite_ref-oka_4-0" class="reference"><a href="#cite_note-oka-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>L'alta reattivià della tioaldeidi può essere diminuita di una certa misura attraverso una stabilizzazione cinetica o termodinamica. Nel primo caso, gruppi sostituenti piuttosto voluminosi in posizione α possono proteggere stericamente le tioaldeidi e permettere l'isolamento delle singola molecole, ne sono un esempio la 2,4,6-tri-terz-butil-tiobenzaldeide<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> e la tris(trimetilsilil) etanotiale.<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> Tra le tioaldeidi termodinamicamente stabilizzate si può invece citare il caso dell'aldeide viniloga 3-dimetilammino-propenetiale in cui la stabilizzazione si ha grazie al contributo della sua forma <a href="/wiki/Risonanza_(chimica)" title="Risonanza (chimica)">risonante</a>. </p> <table> <tbody><tr> <td><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:2,4,6-tri-tert-butylbenzothioaldehyd_V1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/2%2C4%2C6-tri-tert-butylbenzothioaldehyd_V1.svg/220px-2%2C4%2C6-tri-tert-butylbenzothioaldehyd_V1.svg.png" decoding="async" width="220" height="189" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/2%2C4%2C6-tri-tert-butylbenzothioaldehyd_V1.svg/330px-2%2C4%2C6-tri-tert-butylbenzothioaldehyd_V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/2%2C4%2C6-tri-tert-butylbenzothioaldehyd_V1.svg/440px-2%2C4%2C6-tri-tert-butylbenzothioaldehyd_V1.svg.png 2x" data-file-width="401" data-file-height="344" /></a><figcaption>2,4,6-tri-terz-butil-tiobenzaldeide.</figcaption></figure> </td> <td><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Tris(trimetilsilil)etanotiale.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Tris%28trimetilsilil%29etanotiale.jpg/220px-Tris%28trimetilsilil%29etanotiale.jpg" decoding="async" width="220" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/3/32/Tris%28trimetilsilil%29etanotiale.jpg 1.5x" data-file-width="237" data-file-height="163" /></a><figcaption>Tris(trimetilsilil) etanotiale.</figcaption></figure> </td> <td><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:3-dimethylaminothioacrolein.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/3-dimethylaminothioacrolein.png/220px-3-dimethylaminothioacrolein.png" decoding="async" width="220" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/3-dimethylaminothioacrolein.png/330px-3-dimethylaminothioacrolein.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/3-dimethylaminothioacrolein.png/440px-3-dimethylaminothioacrolein.png 2x" data-file-width="1755" data-file-height="479" /></a><figcaption>3-dimetilammino-propenetiale.</figcaption></figure> </td></tr></tbody></table> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Sintesi">Sintesi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tioaldeidi&veaction=edit&section=1" title="Modifica la sezione Sintesi" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Tioaldeidi&action=edit&section=1" title="Edit section's source code: Sintesi"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esistono vari metodi per la sintesi di tioformaldeidi, ognuno preferibile a seconda del tipo di composto che si vuole ottenere.<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> </p><p>Uno dei più comuni è la cicloinversione di composti eterociclici dello zolfo con un anello di quattro elementi attraverso fotolisi o termolisi. Ad esempio, sottoponendo a <a href="/wiki/Fotolisi" title="Fotolisi">fotolisi</a>, ad una temperatura di 10 K, delle molecole di <a href="/w/index.php?title=Triotiocarbonato_di_metilene&action=edit&redlink=1" class="new" title="Triotiocarbonato di metilene (la pagina non esiste)">triotiocarbonato di metilene</a> isolate in una matrice di argon, si è riusciti per la prima volta, nel 1982, ad ottenere delle molecole di <a href="/wiki/Tioformaldeide" title="Tioformaldeide">tioformaldeide</a> stabili.<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> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Triotiocarbonato_di_metilene.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Triotiocarbonato_di_metilene.jpg/400px-Triotiocarbonato_di_metilene.jpg" decoding="async" width="400" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/0/0f/Triotiocarbonato_di_metilene.jpg 1.5x" data-file-width="584" data-file-height="139" /></a><figcaption>Fotolisi del triotiocarbonato di metilene.</figcaption></figure> <p>Il primo ad ottenere una tioaldeide eterociclica stabile fu, nel 1960, Woodward che la ottenne come prodotto intermedio in una sintesi totale di clorofilla facendo reagire un sale di <a href="/wiki/Imminio" title="Imminio">imminio</a> con un idrogenosolfuro basico. Oggi questo metodo è stato esteso ed è diventato uno dei più comuni per ottenere tioaldeidi eterocicliche stabili, che si ottengono quindi dall'utilizzo di <a href="/wiki/Idrogenosolfuro_di_sodio" class="mw-redirect" title="Idrogenosolfuro di sodio">idrogenosolfuro di sodio</a> in <a href="/wiki/Reazione_di_Vilsmeier-Haack" title="Reazione di Vilsmeier-Haack">reazioni di Vilsmeier</a> modificate. Di seguito la sintesi di un'aldeide eterociclica a partire da un pirrolo[2,1-b]-tiazolo. Dal trattamento di questo con <a href="/wiki/Ossicloruro_di_fosforo" title="Ossicloruro di fosforo">ossicloruro di fosforo</a> e <a href="/wiki/Dimetilformammide" title="Dimetilformammide">dimetilformammide</a> si ottiene il sale di Vilsmeier intermedio, e dalla razione di quest'ultimo con <a href="/wiki/Idrogenosolfuro_di_sodio" class="mw-redirect" title="Idrogenosolfuro di sodio">idrogenosolfuro di sodio</a> la corrispondente tioaldeide. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Sintesi_tioaldeide_eterociclica.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Sintesi_tioaldeide_eterociclica.jpg/440px-Sintesi_tioaldeide_eterociclica.jpg" decoding="async" width="440" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Sintesi_tioaldeide_eterociclica.jpg/660px-Sintesi_tioaldeide_eterociclica.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Sintesi_tioaldeide_eterociclica.jpg/880px-Sintesi_tioaldeide_eterociclica.jpg 2x" data-file-width="1705" data-file-height="430" /></a><figcaption>La sintesi di una tioaldeide eterociclica.</figcaption></figure> <p>Un altro metodo prevede la formazione di una tioaldeide attraverso la solforazione del suo corrispettivo carbonilico. Tra i vari reagenti solforizzanti, il più efficace ed utilizzato è l'esametildisilatiano.<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> Ad esempio, se si tratta una miscela di aldeidi e sililalleni con l'esametildisilatiano in presenza di <a href="/wiki/Cloruro_di_cobalto" title="Cloruro di cobalto">cloruro di cobalto</a>, si ottiene le corrispondenti tioaldeidi e i corrispondenti tioacilsilani α,β-insaturi i quali sono poi soggetti in minor parte ad una reazione cicloadditiva che restituisce dei 6-silil-4H-1,3-ditiini 2-sostituiti. </p> <div class="mw-heading mw-heading2"><h2 id="Note">Note</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tioaldeidi&veaction=edit&section=2" title="Modifica la sezione Note" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Tioaldeidi&action=edit&section=2" title="Edit section's source code: Note"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><a href="#cite_ref-1"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/A00208.html"><span style="font-style:italic;">Thioaldehydes</span></a>, su <span style="font-style:italic;">IUPAC Gold Book</span>, IUPAC. <small>URL consultato il 19 settembre 2017</small>.</cite></span> </li> <li id="cite_note-2"><a href="#cite_ref-2"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> H. 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Spagnolo, <a rel="nofollow" class="external text" href="https://oadoi.org/10.1246/cl.1995.147"><span style="font-style:italic;">Synthetic Applications of Bis(trimethylsilyl)sulfide: Part II. Synthesis of Aromatic and Heteroaromatic o-Azido-Thioaldehydes</span></a>, in <span style="font-style:italic;">Chemistry Letters</span>, vol. 24, n. 2, 1995, p. 147, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1246%2Fcl.1995.147">10.1246/cl.1995.147</a>.</cite></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Voci_correlate">Voci correlate</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tioaldeidi&veaction=edit&section=3" title="Modifica la sezione Voci correlate" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Tioaldeidi&action=edit&section=3" title="Edit section's source code: Voci correlate"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Tiochetoni" title="Tiochetoni">Tiochetoni</a></li> <li><a href="/wiki/Tioenoli" title="Tioenoli">Tioenoli</a></li> <li><a href="/w/index.php?title=Composti_organosolforici&action=edit&redlink=1" class="new" title="Composti organosolforici (la pagina non esiste)">Composti organosolforici</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Collegamenti_esterni">Collegamenti esterni</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tioaldeidi&veaction=edit&section=4" title="Modifica la sezione Collegamenti esterni" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Tioaldeidi&action=edit&section=4" title="Edit section's source code: Collegamenti esterni"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li class="mw-empty-elt"></li> <li><cite id="CITEREFBritannica.com" class="citation web" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) <a rel="nofollow" class="external text" href="https://www.britannica.com/science/thioaldehyde"><span style="font-style:italic;">thioaldehyde</span></a>, su <span style="font-style:italic;"><a href="/wiki/Enciclopedia_Britannica" title="Enciclopedia Britannica">Enciclopedia Britannica</a></span>, Encyclopædia Britannica, Inc.</cite> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q1088212#P1417" title="Modifica su Wikidata"><img alt="Modifica su Wikidata" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/10px-Blue_pencil.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/15px-Blue_pencil.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/20px-Blue_pencil.svg.png 2x" data-file-width="600" data-file-height="600" /></a></span></li></ul> <style data-mw-deduplicate="TemplateStyles:r141815314">.mw-parser-output .navbox{border:1px solid #aaa;clear:both;margin:auto;padding:2px;width:100%}.mw-parser-output .navbox th{padding-left:1em;padding-right:1em;text-align:center}.mw-parser-output .navbox>tbody>tr:first-child>th{background:#ccf;font-size:90%;width:100%;color:var(--color-base,black)}.mw-parser-output .navbox_navbar{float:left;margin:0;padding:0 10px 0 0;text-align:left;width:6em}.mw-parser-output .navbox_title{font-size:110%}.mw-parser-output .navbox_abovebelow{background:#ddf;font-size:90%;font-weight:normal}.mw-parser-output .navbox_group{background:#ddf;font-size:90%;padding:0 10px;white-space:nowrap}.mw-parser-output .navbox_list{font-size:90%;width:100%}.mw-parser-output .navbox_list a{white-space:nowrap}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_odd{background:#fdfdfd;color:var(--color-base,black)}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_even{background:#f7f7f7;color:var(--color-base,black)}.mw-parser-output .navbox a.mw-selflink{color:var(--color-base,black)}.mw-parser-output .navbox_center{text-align:center}.mw-parser-output .navbox .navbox_image{padding-left:7px;vertical-align:middle;width:0}.mw-parser-output .navbox+.navbox{margin-top:-1px}.mw-parser-output .navbox .mw-collapsible-toggle{font-weight:normal;text-align:right;width:7em}body.skin--responsive .mw-parser-output .navbox_image img{max-width:none!important}.mw-parser-output .subnavbox{margin:-3px;width:100%}.mw-parser-output .subnavbox_group{background:#e6e6ff;padding:0 10px}@media screen{html.skin-theme-clientpref-night .mw-parser-output .navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-night .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-night .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-os .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-os .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}</style><table class="navbox mw-collapsible mw-collapsed noprint metadata" id="navbox-Gruppi_funzionali"><tbody><tr><th colspan="2"><div class="navbox_navbar"><div class="noprint plainlinks" style="background-color:transparent; padding:0; font-size:xx-small; color:var(--color-base, #000000); white-space:nowrap;"><a href="/wiki/Template:Gruppi_funzionali" title="Template:Gruppi funzionali"><span title="Vai alla pagina del template">V</span></a> · <a href="/w/index.php?title=Discussioni_template:Gruppi_funzionali&action=edit&redlink=1" class="new" title="Discussioni template:Gruppi funzionali (la pagina non esiste)"><span title="Discuti del template">D</span></a> · <a class="external text" href="https://it.wikipedia.org/w/index.php?title=Template:Gruppi_funzionali&action=edit"><span title="Modifica il template. Usa l'anteprima prima di salvare">M</span></a></div></div><span class="navbox_title"><a href="/wiki/Gruppo_funzionale" title="Gruppo funzionale">Gruppi funzionali</a></span></th></tr><tr><th colspan="1" class="navbox_group"><a href="/wiki/Idrocarburi" title="Idrocarburi">Idrocarburi</a> (<a href="/wiki/Carbonio" title="Carbonio">C</a> e <a href="/wiki/Idrogeno" title="Idrogeno">H</a>)</th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Alchile" title="Alchile">Alchile</a> (<a href="/wiki/Metile" title="Metile">Metile</a>, <a href="/wiki/Etile" title="Etile">Etile</a>, <a href="/wiki/Propile" title="Propile">Propile</a>, <a href="/wiki/Butile" title="Butile">Butile</a>, <a href="/wiki/Pentile" title="Pentile">Pentile</a>)<b> ·</b> <a href="/w/index.php?title=Alchenile&action=edit&redlink=1" class="new" title="Alchenile (la pagina non esiste)">Alchenile</a> (<a href="/wiki/Allile" title="Allile">Allile</a>, <a href="/wiki/Gruppo_vinilico" title="Gruppo vinilico">Vinile</a>)<b> ·</b> <a href="/w/index.php?title=Alchinile&action=edit&redlink=1" class="new" title="Alchinile (la pagina non esiste)">Alchinile</a><b> ·</b> <a href="/wiki/Alleni" title="Alleni">Allene</a><b> ·</b> <a href="/wiki/Benzile" title="Benzile">Benzile</a><b> ·</b> <a href="/wiki/Carbene" title="Carbene">Carbene</a><b> ·</b> <a href="/wiki/Carbino" title="Carbino">Carbino</a><b> ·</b> <a href="/wiki/Cumuleni" title="Cumuleni">Cumulene</a><b> ·</b> <a href="/wiki/Metandiile" title="Metandiile">Ponte metilene</a><b> ·</b> <a href="/wiki/Metilidene" title="Metilidene">Metilidene</a><b> ·</b> <a href="/wiki/Metino" title="Metino">Metino</a><b> ·</b> <a href="/wiki/Fenile" title="Fenile">Fenile</a></td></tr><tr><th colspan="1" class="navbox_group">Gruppi con C, H e <a href="/wiki/Ossigeno" title="Ossigeno">O</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Acetossi" title="Acetossi">Acetossi</a><b> ·</b> <a href="/wiki/Acetile" title="Acetile">Acetile</a><b> ·</b> <a href="/wiki/Acriloile" title="Acriloile">Acriloile</a><b> ·</b> <a href="/wiki/Acile" title="Acile">Acile</a><b> ·</b> <a href="/wiki/Acile#Esempi" title="Acile">Formile</a><b> ·</b> <a href="/w/index.php?title=Alcossi&action=edit&redlink=1" class="new" title="Alcossi (la pagina non esiste)">Alcossi</a> (<a href="/wiki/Metossi" title="Metossi">Metossi</a>)<b> ·</b> <a href="/wiki/Benzoile" title="Benzoile">Benzoile</a><b> ·</b> <a href="/wiki/Carbonile" title="Carbonile">Carbonile</a><b> ·</b> <a href="/wiki/Acidi_carbossilici" title="Acidi carbossilici">Carbossile</a><b> ·</b> <a href="/wiki/Diossirano" title="Diossirano">Diossirano</a><b> ·</b> <a href="/wiki/Epossidi" title="Epossidi">Epossidi</a><b> ·</b> <a href="/wiki/Esteri" title="Esteri">Estere</a><b> ·</b> <a href="/wiki/Eteri" title="Eteri">Etere</a><b> ·</b> <a href="/w/index.php?title=Etilendiossi&action=edit&redlink=1" class="new" title="Etilendiossi (la pagina non esiste)">Etilendiossi</a><b> ·</b> <a href="/wiki/Gruppo_ossidrilico" title="Gruppo ossidrilico">Idrossile</a><b> ·</b> <a href="/wiki/Chetoni" title="Chetoni">Chetone</a><b> ·</b> <a href="/wiki/Metilendiossi" title="Metilendiossi">Metilendiossi</a><b> ·</b> <a href="/wiki/Perossidi" title="Perossidi">Perossido</a> (<a href="/w/index.php?title=Perossido_organico&action=edit&redlink=1" class="new" title="Perossido organico (la pagina non esiste)">Organico</a>)<b> ·</b> <a href="/w/index.php?title=Ynone&action=edit&redlink=1" class="new" title="Ynone (la pagina non esiste)">Ynone</a></td></tr><tr><th colspan="1" class="navbox_group">Gruppi con C, H, O <br />e un altro atomo</th><td colspan="1" class="navbox_list navbox_odd"><table class="subnavbox"><tbody><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Azoto" title="Azoto">Azoto</a></th><td colspan="1"><a href="/wiki/Ammine" title="Ammine">Ammina</a><b> ·</b> <a href="/wiki/Azocomposti" title="Azocomposti">Azoico</a><b> ·</b> <a href="/wiki/Cianato" title="Cianato">Cianato</a><b> ·</b> <a href="/wiki/Idrazoni" title="Idrazoni">Idrazone</a><b> ·</b> <a href="/wiki/Immidi" title="Immidi">Immide</a><b> ·</b> <a href="/wiki/Immine" title="Immine">Immina</a><b> ·</b> <a href="/wiki/Isocianati" title="Isocianati">Isocianato</a><b> ·</b> <a href="/wiki/Isocianuri" title="Isocianuri">Isonitrile</a><b> ·</b> <a href="/wiki/Nitrene" title="Nitrene">Nitrene</a><b> ·</b> <a href="/wiki/Nitrili" title="Nitrili">Nitrile</a><b> ·</b> <a href="/wiki/Nitroderivati" title="Nitroderivati">Composto nitro</a><b> ·</b> <a href="/wiki/Nitrosoderivati" title="Nitrosoderivati">Composto nitroso</a><b> ·</b> <a href="/wiki/Ammidi" title="Ammidi">Ammide organica</a><b> ·</b> <a href="/wiki/Ossima" title="Ossima">Ossime</a></td></tr><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Fosforo" title="Fosforo">Fosforo</a></th><td colspan="1"><a href="/wiki/Fosfonati" title="Fosfonati">Fosfonato</a><b> ·</b> <a href="/w/index.php?title=Fosfonite&action=edit&redlink=1" class="new" title="Fosfonite (la pagina non esiste)">Fosfonoso</a></td></tr><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Zolfo" title="Zolfo">Zolfo</a></th><td colspan="1"><a href="/wiki/Disolfuro" title="Disolfuro">Ponte S-S</a><b> ·</b> <a href="/wiki/Solfoni" title="Solfoni">Solfonile</a><b> ·</b> <a href="/wiki/Acidi_solfonici" title="Acidi solfonici">Idrossisolfonile</a><b> ·</b> <a href="/wiki/Solfossidi" title="Solfossidi">Solfenile</a><b> ·</b> <a class="mw-selflink selflink">Tiocarbonile</a><b> ·</b> <a href="/wiki/Tioesteri" title="Tioesteri">Tiocarbossile</a><b> ·</b> <a href="/wiki/Tioeteri" title="Tioeteri">Solfuro</a><b> ·</b> <a href="/w/index.php?title=Tiochetone&action=edit&redlink=1" class="new" title="Tiochetone (la pagina non esiste)">Tiochetone</a><b> ·</b> <a href="/wiki/Tioli" title="Tioli">Tiolo</a></td></tr><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Selenio" title="Selenio">Selenio</a></th><td colspan="1"><a href="/wiki/Selenoli" title="Selenoli">Selenolo</a><b> ·</b> <a href="/w/index.php?title=Acido_selenonico&action=edit&redlink=1" class="new" title="Acido selenonico (la pagina non esiste)">Acido selenonico</a><b> ·</b> <a href="/w/index.php?title=Acido_seleninico&action=edit&redlink=1" class="new" title="Acido seleninico (la pagina non esiste)">Acido seleninico</a><b> ·</b> <a href="/w/index.php?title=Acido_selenenico&action=edit&redlink=1" class="new" title="Acido selenenico (la pagina non esiste)">Acido selenenico</a></td></tr><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Tellurio" title="Tellurio">Tellurio</a></th><td colspan="1"><a href="/wiki/Tellurolo" title="Tellurolo">Tellurolo</a></td></tr></tbody></table></td></tr><tr><th colspan="1" class="navbox_group">Altri gruppi</th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Isotiocianati" title="Isotiocianati">Isotiocianato</a><b> ·</b> <a href="/wiki/Ammidi" title="Ammidi">Fosforoammide</a><b> ·</b> <a href="/w/index.php?title=Cloruoro_sulfenile&action=edit&redlink=1" class="new" title="Cloruoro sulfenile (la pagina non esiste)">Cloruoro sulfenile</a><b> ·</b> <a href="/wiki/Ammidi" title="Ammidi">Solfonoammide</a><b> ·</b> <a href="/wiki/Tiocianato" title="Tiocianato">Tiocianato</a></td></tr><tr><th colspan="2" class="navbox_abovebelow">Vedi anche <i><a href="/w/index.php?title=Classificazione_chimica&action=edit&redlink=1" class="new" title="Classificazione chimica (la pagina non esiste)">Classificazione chimica</a></i>, <i><a href="/wiki/Nomenclatura_chimica" title="Nomenclatura chimica">Nomenclatura chimica</a></i> (<a href="/w/index.php?title=Nomenclatura_IUPAC_dei_composti_inorganici&action=edit&redlink=1" class="new" title="Nomenclatura IUPAC dei composti inorganici (la pagina non esiste)">inorganica</a>, <a href="/wiki/Nomenclatura_IUPAC_dei_composti_organici" title="Nomenclatura IUPAC dei composti organici">organica</a>)</th></tr></tbody></table> <style data-mw-deduplicate="TemplateStyles:r140554510">.mw-parser-output .CdA{border:1px solid #aaa;width:100%;margin:auto;font-size:90%;padding:2px}.mw-parser-output .CdA th{background-color:#f2f2f2;font-weight:bold;width:20%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .CdA{border-color:#54595D}html.skin-theme-clientpref-night .mw-parser-output .CdA th{background-color:#202122}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .CdA{border-color:#54595D}html.skin-theme-clientpref-os .mw-parser-output .CdA th{background-color:#202122}}</style><table class="CdA"><tbody><tr><th><a href="/wiki/Aiuto:Controllo_di_autorit%C3%A0" title="Aiuto:Controllo di autorità">Controllo di autorità</a></th><td><a href="/wiki/Gemeinsame_Normdatei" title="Gemeinsame Normdatei">GND</a> <span class="uid">(<span style="font-weight:bolder; font-size:80%"><abbr title="tedesco">DE</abbr></span>) <a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4313246-7">4313246-7</a></span></td></tr></tbody></table> <div class="noprint" style="width:100%; padding: 3px 0; display: flex; flex-wrap: wrap; row-gap: 4px; column-gap: 8px; box-sizing: border-box;"><div style="flex-grow: 1"><style data-mw-deduplicate="TemplateStyles:r140555418">.mw-parser-output .itwiki-template-occhiello{width:100%;line-height:25px;border:1px solid #CCF;background-color:#F0EEFF;box-sizing:border-box}.mw-parser-output .itwiki-template-occhiello-progetto{background-color:#FAFAFA}@media screen{html.skin-theme-clientpref-night .mw-parser-output .itwiki-template-occhiello{background-color:#202122;border-color:#54595D}html.skin-theme-clientpref-night .mw-parser-output .itwiki-template-occhiello-progetto{background-color:#282929}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .itwiki-template-occhiello{background-color:#202122;border-color:#54595D}html.skin-theme-clientpref-os .mw-parser-output .itwiki-template-occhiello-progetto{background-color:#282929}}</style><div class="itwiki-template-occhiello"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Gnome-applications-science.svg" class="mw-file-description" title="Chimica"><img alt=" " src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Gnome-applications-science.svg/25px-Gnome-applications-science.svg.png" decoding="async" width="25" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Gnome-applications-science.svg/38px-Gnome-applications-science.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Gnome-applications-science.svg/50px-Gnome-applications-science.svg.png 2x" data-file-width="48" data-file-height="48" /></a></span> <b><a href="/wiki/Portale:Chimica" title="Portale:Chimica">Portale Chimica</a></b>: il portale della scienza della composizione, delle proprietà e delle trasformazioni della materia</div></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&useformat=desktop" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Estratto da "<a dir="ltr" href="https://it.wikipedia.org/w/index.php?title=Tioaldeidi&oldid=135340057">https://it.wikipedia.org/w/index.php?title=Tioaldeidi&oldid=135340057</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Categoria:Categorie" title="Categoria:Categorie">Categorie</a>: <ul><li><a href="/wiki/Categoria:Gruppi_funzionali" title="Categoria:Gruppi funzionali">Gruppi funzionali</a></li><li><a href="/wiki/Categoria:Tioaldeidi" title="Categoria:Tioaldeidi">Tioaldeidi</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks 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