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class="infobox ib-reactionbox"> <tbody><tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Wulff–Dötz reaction </th></tr> <tr> <td>Named after </td> <td><a href="/wiki/William_Wulff" title="William Wulff">William Wulff</a><br />Karl Heinz Dötz </td></tr> <tr> <td>Reaction type </td> <td><a href="/wiki/Ring_forming_reaction" title="Ring forming reaction">Ring forming reaction</a> </td></tr> <tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Identifiers </th></tr> <tr> <td><a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a> ontology ID </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/ols/ontologies/rxno/terms?iri=http%3A%2F%2Fpurl.obolibrary.org%2Fobo%2FRXNO_0000681">RXNO:0000681</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <p>The <b>Wulff–Dötz reaction</b> (also known as the <b>Dötz reaction</b> or the benzannulation reaction of the <a href="/wiki/Fischer_carbene" title="Fischer carbene">Fischer carbene</a> complexes) is the <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> of an <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> or vinylic <a href="/wiki/Alkoxy" class="mw-redirect" title="Alkoxy">alkoxy</a> pentacarbonyl <a href="/wiki/Chromium" title="Chromium">chromium</a> <a href="/wiki/Transition_metal_carbene_complex" title="Transition metal carbene complex">carbene complex</a> with an <a href="/wiki/Alkyne" title="Alkyne">alkyne</a> and <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> to give a Cr(CO)<sub>3</sub>-coordinated substituted <a href="/wiki/Phenol" title="Phenol">phenol</a>.<sup id="cite_ref-Dötz1975_1-0" class="reference"><a href="#cite_note-Dötz1975-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dötz1976_2-0" class="reference"><a href="#cite_note-Dötz1976-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Timko1339_3-0" class="reference"><a href="#cite_note-Timko1339-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Several reviews have been published.<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><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> It is named after the German chemist Karl Heinz Dötz (b. 1943) and the American chemist William D. Wulff (b. 1949) at Michigan State University.<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> The reaction was first discovered by Karl Dötz and was extensively developed by his group and W. Wulff's group. They subsequently share the name of the reaction. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Wulffdotz3.png" class="mw-file-description" title="The Dötz reaction"><img alt="The Dötz reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Wulffdotz3.png/400px-Wulffdotz3.png" decoding="async" width="400" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Wulffdotz3.png/600px-Wulffdotz3.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Wulffdotz3.png/800px-Wulffdotz3.png 2x" data-file-width="1287" data-file-height="388" /></a><figcaption>The Dötz reaction</figcaption></figure> <p>The position of the substituents is highly predictable with the largest alkyne substituent (R<sub>L</sub>) neighboring the phenol and the smallest alkyne substituent (R<sub>S</sub>) neighboring the methoxy group.<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><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> Hence, this reaction is more useful for terminal alkynes than internal alkynes. </p><p>The phenol can be liberated from the chromium complex by a mild <a href="/wiki/Redox" title="Redox">oxidation</a>, such as <a href="/wiki/Ammonium_cerium(IV)_nitrate" class="mw-redirect" title="Ammonium cerium(IV) nitrate">ceric ammonium nitrate</a> or air oxidation. </p><p>Since this reaction can quickly generate complex phenolic compounds, the Wulff–Dötz reaction has been used most often in the synthesis of <a href="/wiki/Natural_product" title="Natural product">natural products</a>, especially <a href="/wiki/Vitamin_E" title="Vitamin E">Vitamins E</a> and <a href="/wiki/Vitamin_K" title="Vitamin K">K</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is also applicable to the synthesis of polyphenolic compounds, such as <a href="/wiki/Calixarene" title="Calixarene">calixarenes</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Mechanism">Mechanism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Wulff%E2%80%93D%C3%B6tz_reaction&action=edit&section=1" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The mechanism is thought to begin with the loss of <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> from the <a href="/wiki/Fischer_carbene" title="Fischer carbene">Fischer carbene</a> complex <b>1</b> to give intermediate <b>3</b>. The loss of CO is rate limiting making the investigation of this reaction mechanism difficult, since all subsequent steps occur rapidly. The alkyne then coordinates to the metal center, a low-energy barrier process. The resulting <a href="/wiki/Alkyne_complex" class="mw-redirect" title="Alkyne complex">alkyne complex</a> rearranges to intermediate <b>4</b>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The η<sup>1</sup>, η<sup>3</sup>-complex shown as <b>4</b> subsequently undergoes CO insertion to give the η<sup>4</sup>-vinylketene complex <b>5</b>, which undergoes <a href="/wiki/Electrocyclization" class="mw-redirect" title="Electrocyclization">electrocyclization</a> to give intermediate <b>6</b>. When R<sub>1</sub> is hydrogen, intermediate <b>6</b> is short lived and proceeds to the metal tricarbonyl arene complex <b>2</b>. Without CO insertion, the reaction proceeds through <b>7</b> to the <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> product <b>8</b>. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Wulffmechanism3.png" class="mw-file-description" title="The Dötz reaction"><img alt="The Dötz reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Wulffmechanism3.png/600px-Wulffmechanism3.png" decoding="async" width="600" height="530" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Wulffmechanism3.png/900px-Wulffmechanism3.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/28/Wulffmechanism3.png/1200px-Wulffmechanism3.png 2x" data-file-width="1823" data-file-height="1611" /></a><figcaption>The Dötz reaction</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Examples">Examples</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Wulff%E2%80%93D%C3%B6tz_reaction&action=edit&section=2" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Exposing <a href="/wiki/Fischer_carbene" title="Fischer carbene">Fischer carbene</a> with alkenyl side chain to an alkyne gives a highly substituted phenol. The phenolic carbon is originated from the CO ligand. The α,β-unsaturated part could also be from an electron rich aryl system, yielding a polycyclic aromatic system. This reaction was first discovered by Karl Dötz and was extensively developed by his group, thus giving the name Dötz reaction. It is sometimes called Wuff-Dötz reaction because William Wuff's group at Michigan State University also extensively contributed to the development of this reaction.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Dotz_1.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/4/47/Dotz_1.jpg" decoding="async" width="696" height="436" class="mw-file-element" data-file-width="696" data-file-height="436" /></a></span></dd></dl> <p>The half-sandwich complex in the Dötz reaction can be demetallated to give corresponding aryl product, or it could be further employed for a nucleophilic addition to aromatic system strategy for synthesis of fully-substituted benzene ring.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Dotz_2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/8/82/Dotz_2.jpg" decoding="async" width="855" height="365" class="mw-file-element" data-file-width="855" data-file-height="365" /></a></span></dd></dl> <p>The Dötz reaction has been employed in the syntheses of natural products, as illustrated below.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Dotz_4.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/d/d8/Dotz_4.jpg" decoding="async" width="761" height="322" class="mw-file-element" data-file-width="761" data-file-height="322" /></a></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Interrupted_Dötz_reaction"><span id="Interrupted_D.C3.B6tz_reaction"></span>Interrupted Dötz reaction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Wulff%E2%80%93D%C3%B6tz_reaction&action=edit&section=3" title="Edit section: Interrupted Dötz reaction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In several cases, if the reactivity of the reagent does not meet or the conditions for Dotz mechanism to operate are not fulfilled, products derived from the interrupted Dotz reaction could be dominant. For instance, if the substituents on alkyne are too bulky, cyclobutene product would be observed instead.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Interrupted_1.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/f/f9/Interrupted_1.jpg" decoding="async" width="715" height="108" class="mw-file-element" data-file-width="715" data-file-height="108" /></a></span> </p><p>If the alkyne partner bearing a ketone substituent and both R and R’ are not bulky enough, a favored conformation for an 8e pi cyclization could be dominant leading to a fused bicyclic lactone system.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Interrupted_2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/2/2e/Interrupted_2.jpg" decoding="async" width="766" height="327" class="mw-file-element" data-file-width="766" data-file-height="327" /></a></span> </p><p>Alkene or nucleophilic moiety on the side chain of alkyne partner could trap the resulting ketene through a [2+2] cycloaddition or nucleophilic addition respectively. This strategy was applied for the syntheses of blastmycinone and antimycinone.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Interrupted_3.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/b/bf/Interrupted_3.jpg" decoding="async" width="786" height="138" class="mw-file-element" data-file-width="786" data-file-height="138" /></a></span> <span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Interrupted_4.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/a/ac/Interrupted_4.jpg" decoding="async" width="853" height="173" class="mw-file-element" data-file-width="853" data-file-height="173" /></a></span> </p><p>Fischer carbenes with an α-hydrogen could form could give cyclopentenone product similar to Pauson-Khand reaction. This is presumably because of a β-hydride elimination and reinsertion process.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Interrupted_5.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/4/42/Interrupted_5.jpg" decoding="async" width="685" height="259" class="mw-file-element" data-file-width="685" data-file-height="259" /></a></span> </p><p>If the alkene moiety is present in Fischer carbene, but not in conjugation, cyclopropanation could be observed. The strategy was employed in a formal synthesis of carabrone.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Interrupted_6.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/e/e7/Interrupted_6.jpg" decoding="async" width="853" height="151" class="mw-file-element" data-file-width="853" data-file-height="151" /></a></span> <span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Interrupted_7.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/3/3b/Interrupted_7.jpg" decoding="async" width="638" height="323" class="mw-file-element" data-file-width="638" data-file-height="323" /></a></span> </p><p><br /> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Wulff%E2%80%93D%C3%B6tz_reaction&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Dötz1975-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Dötz1975_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFDötz1975" class="citation journal cs1">Dötz, Karl Heinz (September 1975). "Synthesis of the Naphthol Skeleton from Pentacarbonyl-[methoxy(phenyl)carbene]chromium (O) and Tolan". <i>Angewandte Chemie International Edition in English</i>. <b>14</b> (9): 644–645. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.197506442">10.1002/anie.197506442</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition+in+English&rft.atitle=Synthesis+of+the+Naphthol+Skeleton+from+Pentacarbonyl-%5Bmethoxy%28phenyl%29carbene%5Dchromium+%28O%29+and+Tolan&rft.volume=14&rft.issue=9&rft.pages=644-645&rft.date=1975-09&rft_id=info%3Adoi%2F10.1002%2Fanie.197506442&rft.aulast=D%C3%B6tz&rft.aufirst=Karl+Heinz&rfr_id=info%3Asid%2Fen.wikipedia.org%3AWulff%E2%80%93D%C3%B6tz+reaction" class="Z3988"></span></span> </li> <li id="cite_note-Dötz1976-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Dötz1976_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHeinz_DötzDietzvon_ImhofLorenz1976" class="citation journal cs1">Heinz Dötz, Karl; Dietz, Robert; von Imhof, Alexander; Lorenz, Hans; Huttner, Gottfried (June 1976). "Reaktionen von Komplexliganden, IV. Stereoselektive Synthese substituierter Naphthaline: Darstellung und Struktur eines Tricarbonyl(naphthalin)chrom(0)-Komplexes". <i>Chemische Berichte</i>. <b>109</b> (6): 2033–2038. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.19761090610">10.1002/cber.19761090610</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemische+Berichte&rft.atitle=Reaktionen+von+Komplexliganden%2C+IV.+Stereoselektive+Synthese+substituierter+Naphthaline%3A+Darstellung+und+Struktur+eines+Tricarbonyl%28naphthalin%29chrom%280%29-Komplexes&rft.volume=109&rft.issue=6&rft.pages=2033-2038&rft.date=1976-06&rft_id=info%3Adoi%2F10.1002%2Fcber.19761090610&rft.aulast=Heinz+D%C3%B6tz&rft.aufirst=Karl&rft.au=Dietz%2C+Robert&rft.au=von+Imhof%2C+Alexander&rft.au=Lorenz%2C+Hans&rft.au=Huttner%2C+Gottfried&rfr_id=info%3Asid%2Fen.wikipedia.org%3AWulff%E2%80%93D%C3%B6tz+reaction" class="Z3988"></span></span> </li> <li id="cite_note-Timko1339-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Timko1339_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTimkoYamashita1993" class="citation journal cs1">Timko, M.; Yamashita, Ayako (1993). "Synthesis of 2-Substituted Naphthalenediol Derivatives Using Chromium Carbene Complexes: 1-Acetoxy-2-Butyl-4-Methoxynaphthalene". <i>Org. Synth</i>. <b>71</b>: 72. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.071.0072">10.15227/orgsyn.071.0072</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Org.+Synth.&rft.atitle=Synthesis+of+2-Substituted+Naphthalenediol+Derivatives+Using+Chromium+Carbene+Complexes%3A+1-Acetoxy-2-Butyl-4-Methoxynaphthalene&rft.volume=71&rft.pages=72&rft.date=1993&rft_id=info%3Adoi%2F10.15227%2Forgsyn.071.0072&rft.aulast=Timko&rft.aufirst=M.&rft.au=Yamashita%2C+Ayako&rfr_id=info%3Asid%2Fen.wikipedia.org%3AWulff%E2%80%93D%C3%B6tz+reaction" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWatersWilliam2008" class="citation journal cs1">Waters, Marcey; William, Wulff (2008). 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