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Reaction</span> </div> </a> <ul id="toc-Wulff-Dötz_Reaction-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>References</span> 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<div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Class of organometalic compounds</div> <p>A <b>transition metal carbene complex</b> is an <a href="/wiki/Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compound</a> featuring a <a href="/wiki/Divalent" class="mw-redirect" title="Divalent">divalent</a> carbon <a href="/wiki/Ligand" title="Ligand">ligand</a>, itself also called a <a href="/wiki/Carbene" title="Carbene">carbene</a>.<sup id="cite_ref-:3_1-0" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Carbene complexes have been synthesized from most <a href="/wiki/Transition_metal" title="Transition metal">transition metals</a> and <a href="/wiki/Block_(periodic_table)#f-block" title="Block (periodic table)">f-block metals</a>,<sup id="cite_ref-:4_2-0" class="reference"><a href="#cite_note-:4-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> using many different synthetic routes such as nucleophilic addition and alpha-hydrogen abstraction.<sup id="cite_ref-:3_1-1" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The term carbene ligand is a formalism since many are not directly derived from carbenes and most are much less reactive than lone carbenes.<sup id="cite_ref-:4_2-1" class="reference"><a href="#cite_note-:4-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Described often as <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">=CR<sub class="template-chem2-sub">2</sub></span>, carbene ligands are intermediate between alkyls <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">(−CR<sub class="template-chem2-sub">3</sub>)</span> and carbynes <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">(≡CR)</span>. Many different carbene-based reagents such as <a href="/wiki/Tebbe%27s_reagent" title="Tebbe's reagent">Tebbe's reagent</a> are used in synthesis. They also feature in catalytic reactions, especially <a href="/wiki/Alkene_metathesis" class="mw-redirect" title="Alkene metathesis">alkene metathesis</a>, and are of value in both industrial heterogeneous and in homogeneous catalysis for laboratory- and industrial-scale preparation of fine chemicals.<sup id="cite_ref-:3_1-2" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:5_3-0" class="reference"><a href="#cite_note-:5-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:6_4-0" class="reference"><a href="#cite_note-:6-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=1" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metal carbene complexes are often classified into two types. The <b>Fischer carbenes,</b> named after <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Ernst Otto Fischer</a>, feature strong π-acceptors at the metal and are <a href="/wiki/Electrophile" title="Electrophile">electrophilic</a> at the carbene carbon atom. <b>Schrock carbenes</b>, named after <a href="/wiki/Richard_R._Schrock" title="Richard R. Schrock">Richard R. Schrock</a>, are characterized by more nucleophilic carbene carbon centers; these species typically feature higher <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> (valency) metals. <a href="/wiki/N-heterocyclic_carbene" class="mw-redirect" title="N-heterocyclic carbene"><i>N</i>-Heterocyclic carbenes</a> (NHCs) were popularized following Arduengo's isolation of a stable free carbene in 1991.<sup id="cite_ref-arduengo2_5-0" class="reference"><a href="#cite_note-arduengo2-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Reflecting the growth of the area, carbene complexes are now known with a broad range of different reactivities and diverse substituents. Often it is not possible to classify a carbene complex solely with regards to its electrophilicity or nucleophilicity.<sup id="cite_ref-:3_1-3" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fischer_carbenes">Fischer carbenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=2" title="Edit section: Fischer carbenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Fischer_carbene" title="Fischer carbene">Fischer carbene</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Fisher_Carbene_2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Fisher_Carbene_2.png/220px-Fisher_Carbene_2.png" decoding="async" width="220" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Fisher_Carbene_2.png/330px-Fisher_Carbene_2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/d/d5/Fisher_Carbene_2.png 2x" data-file-width="342" data-file-height="242" /></a><figcaption>Example Fisher carbene with chromium(0) centre and diethylamine donor.</figcaption></figure> <p>The common features of Fisher carbenes are:<sup id="cite_ref-:1_6-0" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <ul><li>low <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> metal center</li> <li>middle and late transition metals <a href="/wiki/Iron" title="Iron">Fe(0)</a>, <a href="/wiki/Molybdenum" title="Molybdenum">Mo(0)</a>, <a href="/wiki/Chromium" title="Chromium">Cr(0)</a></li> <li><a href="/wiki/Pi_electron" class="mw-redirect" title="Pi electron">π</a>-acceptor metal <a href="/wiki/Ligand" title="Ligand">ligands</a></li> <li>π-donor <a href="/wiki/Substituent" title="Substituent">substituents</a> on the <a href="/wiki/Carbene" title="Carbene">carbene</a> atom such as <a href="/wiki/Alkoxy" class="mw-redirect" title="Alkoxy">alkoxy</a> and alkylated <a href="/wiki/Amino" class="mw-redirect" title="Amino">amino</a> groups.</li></ul> <p>Examples include <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">(CO)<sub class="template-chem2-sub">5</sub>W=COMePh</span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">(OC)<sub class="template-chem2-sub">5</sub>Cr=C(NR<sub class="template-chem2-sub">2</sub>)Ph</span>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Fisher_Orbitals.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Fisher_Orbitals.png/220px-Fisher_Orbitals.png" decoding="async" width="220" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Fisher_Orbitals.png/330px-Fisher_Orbitals.png 1.5x, //upload.wikimedia.org/wikipedia/commons/4/47/Fisher_Orbitals.png 2x" data-file-width="434" data-file-height="302" /></a><figcaption>Orbital interaction in a Fisher carbene. The carbene electrons are donated to a sigma bond, and weak pi-backbonding occurs.</figcaption></figure> <p>Fisher carbene complexes are related to the singlet form of carbenes, where both electrons occupy the same sp<sup>2</sup> orbital at the carbon. This lone pair donates to a metal-based empty d orbital, forming a σ bond. π-backbonding from a filled metal d orbital to the empty p orbital of the carbon atom is possible. However this interaction is generally weak since the alpha donor atoms also donate to this orbital. As such, fisher carbenes are characterized as having partial double bond character. The major resonance structures of Fisher carbenes put the negative charge on the metal centre, and the positive on the carbon atom, making it electrophilic.<sup id="cite_ref-:1_6-1" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Fisher_Resonance_V2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Fisher_Resonance_V2.png/523px-Fisher_Resonance_V2.png" decoding="async" width="523" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Fisher_Resonance_V2.png/785px-Fisher_Resonance_V2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/5/56/Fisher_Resonance_V2.png 2x" data-file-width="856" data-file-height="137" /></a><figcaption>Major resonance structures of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">(CO)<sub class="template-chem2-sub">5</sub>W=COMePh</span>. Structures with a positive charge on carbon are significant and make the carbon electrophilic.</figcaption></figure> <p>Fischer carbenes can be likened to ketones, with the carbene carbon atom being electrophilic, like the carbonyl carbon atom of a ketone. This can be seen from the <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance structures</a>, where there is a significant contribution from the structure bearing a positive carbon centre.<sup id="cite_ref-:1_6-2" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Like ketones, Fischer carbene species can undergo <a href="/wiki/Aldol_reaction" title="Aldol reaction">aldol</a>-like reactions. The hydrogen atoms attached to the carbon atom α to the carbene carbon atom are acidic, and can be deprotonated by a base such as <a href="/wiki/N-Butyllithium" title="N-Butyllithium"><i>n</i>-butyllithium</a>, to give a nucleophile, which can undergo further reaction.<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> <div class="mw-heading mw-heading3"><h3 id="Schrock_carbenes">Schrock carbenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=3" title="Edit section: Schrock carbenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:CSD_CIF_CPMTAA10.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/CSD_CIF_CPMTAA10.png/220px-CSD_CIF_CPMTAA10.png" decoding="async" width="220" height="247" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/CSD_CIF_CPMTAA10.png/330px-CSD_CIF_CPMTAA10.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/CSD_CIF_CPMTAA10.png/440px-CSD_CIF_CPMTAA10.png 2x" data-file-width="1405" data-file-height="1575" /></a><figcaption>Structure of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>TaCH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)</span>, as determined by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>.<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> The <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">Ta−CH<sub class="template-chem2-sub">3</sub> and Ta=CH<sub class="template-chem2-sub">2</sub></span> distances are 2.37 and 2.04 Å, respectively. Color code: blue = Ta, gray = C, white = H.</figcaption></figure> <p>Schrock carbenes do not have π-accepting ligands on the metal centre. They are often called <b>alkylidene complexes</b>. Typically this subset of carbene complexes are found with:<sup id="cite_ref-:1_6-3" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <ul><li>high <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> metal center</li> <li>early transition metals <a href="/wiki/Titanium" title="Titanium">Ti(IV)</a>, <a href="/wiki/Tantalum" title="Tantalum">Ta(V)</a></li> <li>σ-donor and sometimes π-donor metal ligands</li> <li>hydrogen and alkyl substituents on carbenoid carbon.</li></ul> <p>Examples include <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">((CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>CCH<sub class="template-chem2-sub">2</sub>)Ta=CHC(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span><sup id="cite_ref-:2_9-0" class="reference"><a href="#cite_note-:2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">Os(PPh<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>(NO)Cl(=CH<sub class="template-chem2-sub">2</sub>)</span>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Schrock_Orbitals.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Schrock_Orbitals.png/220px-Schrock_Orbitals.png" decoding="async" width="220" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Schrock_Orbitals.png/330px-Schrock_Orbitals.png 1.5x, //upload.wikimedia.org/wikipedia/commons/f/fe/Schrock_Orbitals.png 2x" data-file-width="434" data-file-height="302" /></a><figcaption>Orbital interaction in the bonding of a Schrock carbene. Both the metal and carbon provide 2 unpaired electron each, forming the double bond.</figcaption></figure> <p>Bonding in such complexes can be viewed as the coupling of a triplet state metal and triplet carbene, forming a true double bond. Both the metal and carbon atom donate 2 electrons, one to each bond. Since there is no donation to the carbene atom from adjacent groups, the extent of <a href="/wiki/Pi_backbonding" title="Pi backbonding">pi backbonding</a> is much greater, giving a strong double bond. These bonds are weakly polarized towards carbon and therefore the carbene atom is a nucleophile. Furthermore, the major resonance structures of Schrock carbene put the negative charge on the carbon atom, making it nucleophilic.<sup id="cite_ref-:1_6-4" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Complexes with the <a href="/wiki/Methylidene_group" class="mw-redirect" title="Methylidene group">methylidene</a> ligand (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">=CH<sub class="template-chem2-sub">2</sub></span>) are the simplest Schrock-type carbenes. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Schrock_Resonance_V2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Schrock_Resonance_V2.png/412px-Schrock_Resonance_V2.png" decoding="async" width="412" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/c/cc/Schrock_Resonance_V2.png 1.5x" data-file-width="452" data-file-height="134" /></a><figcaption>Major resonance structures of a Schrock carbene. The negative charge at the carbon atom renders it nucleophilic.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="N-Heterocyclic_carbenes"><i>N</i>-Heterocyclic carbenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=4" title="Edit section: N-Heterocyclic carbenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene_(aka_IMes).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/1%2C3-bis%282%2C4%2C6-trimethylphenyl%29imidazol-2-ylidene_%28aka_IMes%29.png/220px-1%2C3-bis%282%2C4%2C6-trimethylphenyl%29imidazol-2-ylidene_%28aka_IMes%29.png" decoding="async" width="220" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/1%2C3-bis%282%2C4%2C6-trimethylphenyl%29imidazol-2-ylidene_%28aka_IMes%29.png/330px-1%2C3-bis%282%2C4%2C6-trimethylphenyl%29imidazol-2-ylidene_%28aka_IMes%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/1%2C3-bis%282%2C4%2C6-trimethylphenyl%29imidazol-2-ylidene_%28aka_IMes%29.png/440px-1%2C3-bis%282%2C4%2C6-trimethylphenyl%29imidazol-2-ylidene_%28aka_IMes%29.png 2x" data-file-width="1075" data-file-height="286" /></a><figcaption><a href="/wiki/IMes" title="IMes">IMes</a> is a common NHC ligand.</figcaption></figure><p><a href="/wiki/N-heterocyclic_carbene" class="mw-redirect" title="N-heterocyclic carbene"><i>N</i>-Heterocyclic carbenes</a> (NHCs) are particularly common carbene ligands.<sup id="cite_ref-Hahn3_11-0" class="reference"><a href="#cite_note-Hahn3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> They are popular because they are more readily prepared than Schrock and Fischer carbenes. In fact, many NHCs are isolated as the free ligand, since they are <a href="/wiki/Persistent_carbene" title="Persistent carbene">persistent carbenes</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><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> Being strongly stabilized by π-donating substituents, NHCs are powerful σ-donors but π-bonding with the metal is weak.<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> For this reason, the bond between the carbon and the metal center is often represented by a single dative bond, whereas Fischer and Schrock carbenes are usually depicted with double bonds to metal. Continuing with this analogy, NHCs are often compared with trialkyl<a href="/wiki/Phosphine" title="Phosphine">phosphine</a> ligands. Like phosphines, NHCs serve as <a href="/wiki/Spectator_ligand" title="Spectator ligand">spectator ligands</a> that influence catalysis through a combination of electronic and steric effects, but they do not directly bind substrates.<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><div class="mw-heading mw-heading3"><h3 id="Bimetallic_carbene_complexes">Bimetallic carbene complexes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=5" title="Edit section: Bimetallic carbene complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An early example of this bonding mode was provided by <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">[C<sub class="template-chem2-sub">5</sub>Me<sub class="template-chem2-sub">5</sub>Mn(CO)<sub class="template-chem2-sub">2</sub>]<sub class="template-chem2-sub">2</sub>(μ−CO)</span> prepared from <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">2 C<sub class="template-chem2-sub">5</sub>Me<sub class="template-chem2-sub">5</sub>Mn(CO)<sub class="template-chem2-sub">2</sub>(thf) + CH<sub class="template-chem2-sub">2</sub>N<sub class="template-chem2-sub">2</sub> → [C<sub class="template-chem2-sub">5</sub>Me<sub class="template-chem2-sub">5</sub>Mn(CO)<sub class="template-chem2-sub">2</sub>]<sub class="template-chem2-sub">2</sub>(μ−CH<sub class="template-chem2-sub">2</sub>] + N<sub class="template-chem2-sub">2</sub> + 2 thf</span></dd></dl> <p>Another example of this family of compounds is <a href="/wiki/Tebbe%27s_reagent" title="Tebbe's reagent">Tebbe's reagent</a>. It features a methylene bridge joining <a href="/wiki/Titanium" title="Titanium">titanium</a> and <a href="/wiki/Aluminum" class="mw-redirect" title="Aluminum">aluminum</a>.<sup id="cite_ref-Herrmann_17-0" class="reference"><a href="#cite_note-Herrmann-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Application_of_Metal_Carbenes">Application of Metal Carbenes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=6" title="Edit section: Application of Metal Carbenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metal carbene complexes have applications in hetereogeneous and homogeneous catalysis, and as reagents for organic reactions. </p> <div class="mw-heading mw-heading3"><h3 id="Catalysis">Catalysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=7" title="Edit section: Catalysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Olefin_Metathesis_Catalytic_Cycle.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Olefin_Metathesis_Catalytic_Cycle.png/262px-Olefin_Metathesis_Catalytic_Cycle.png" decoding="async" width="262" height="238" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Olefin_Metathesis_Catalytic_Cycle.png/393px-Olefin_Metathesis_Catalytic_Cycle.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Olefin_Metathesis_Catalytic_Cycle.png/524px-Olefin_Metathesis_Catalytic_Cycle.png 2x" data-file-width="530" data-file-height="482" /></a><figcaption>Catalytic cycle of olefin metathesis. The metal complex alternated between a metallocyclobutane ring and carbene complex, catalyzing the formation of new carbon-carbon double bonds.</figcaption></figure> <p>The dominant application of metal carbenes involves none of the above classes of compounds, but rather <a href="/wiki/Heterogeneous_catalyst" class="mw-redirect" title="Heterogeneous catalyst">heterogeneous catalysts</a> used for <a href="/wiki/Alkene_metathesis" class="mw-redirect" title="Alkene metathesis">alkene metathesis</a> for the synthesis of higher alkenes. A variety of related reactions are used to interconvert light alkenes, e.g. butenes, propylene, and ethylene.<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> Carbene complexes are invoked as intermediates in the <a href="/wiki/Fischer%E2%80%93Tropsch" class="mw-redirect" title="Fischer–Tropsch">Fischer–Tropsch</a> route to hydrocarbons.<sup id="cite_ref-:5_3-1" class="reference"><a href="#cite_note-:5-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>A variety of homogeneous carbene catalysts, especially the <a href="/wiki/Grubbs%27_catalyst" class="mw-redirect" title="Grubbs' catalyst">Grubbs' ruthenium</a> and Schrock molybdenum-imido catalysts have been used for olefin metathesis in laboratory-scale <a href="/wiki/Organic_synthesis" title="Organic synthesis">synthesis</a> of <a href="/wiki/Natural_product" title="Natural product">natural products</a> and <a href="/wiki/Materials_science" title="Materials science">materials science</a>.<sup id="cite_ref-:6_4-1" class="reference"><a href="#cite_note-:6-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Stoichiometric_reactions">Stoichiometric reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=8" title="Edit section: Stoichiometric reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Homogeneous Schrock-type carbene complexes such as <a href="/wiki/Tebbe%27s_reagent" title="Tebbe's reagent">Tebbe's reagent</a> can be used for the olefination of carbonyls, replacing the oxygen atom with a methylidene group. The nucleophilic carbon atom behaves similarly to the carbon atom of the phosphorus ylide in the <a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a>, attacking the electrophilic carbonyl atom of a ketone, followed by elimination of a metal oxide.<sup id="cite_ref-:3_1-4" class="reference"><a href="#cite_note-:3-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Tebbe%27s_Reaction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Tebbe%27s_Reaction.png/442px-Tebbe%27s_Reaction.png" decoding="async" width="442" height="143" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Tebbe%27s_Reaction.png/663px-Tebbe%27s_Reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/a/a0/Tebbe%27s_Reaction.png 2x" data-file-width="803" data-file-height="260" /></a><figcaption>Olefination of an ester using Tebbe's reagent as a methylidene source.</figcaption></figure> <p>In the <a href="/wiki/Nucleophilic_abstraction" title="Nucleophilic abstraction">nucleophilic abstraction</a> reaction, a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> can be abstracted from the donating group of a Fischer carbene, making it a strong nucleophile for further reaction.<sup id="cite_ref-:1_6-5" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Abstraction_Reaction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Abstraction_Reaction.png/584px-Abstraction_Reaction.png" decoding="async" width="584" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Abstraction_Reaction.png/876px-Abstraction_Reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/9/9c/Abstraction_Reaction.png 2x" data-file-width="1079" data-file-height="173" /></a><figcaption>Nucleophilic abstraction of the methyl group of a Fisher carbene. The negatively charge oxygen is a nucleophile which can undergo further reaction.</figcaption></figure> <p>Diazo compounds like <a href="/wiki/Methyl_phenyldiazoacetate" title="Methyl phenyldiazoacetate">methyl phenyldiazoacetate</a> can be used for cyclopropanation or to insert into C-H bonds of organic substrates. These reactions are catalyzed by <a href="/wiki/Dirhodium_tetraacetate" class="mw-redirect" title="Dirhodium tetraacetate">dirhodium tetraacetate</a> or related chiral derivatives. Such catalysis is assumed to proceed via the intermediacy of carbene complexes.<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> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Diazo_C-H_Insertion.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Diazo_C-H_Insertion.png/419px-Diazo_C-H_Insertion.png" decoding="async" width="419" height="249" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Diazo_C-H_Insertion.png/629px-Diazo_C-H_Insertion.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Diazo_C-H_Insertion.png/838px-Diazo_C-H_Insertion.png 2x" data-file-width="866" data-file-height="514" /></a><figcaption>Catalytic cycle for the insertion of carbenes into carbon-hydrogen bonds. The metal carbene is generated by nitrogen elimination from the diazo compound, and then inserts into the C-H bond.</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Wulff-Dötz_Reaction"><span id="Wulff-D.C3.B6tz_Reaction"></span>Wulff-Dötz Reaction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=9" title="Edit section: Wulff-Dötz Reaction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fischer carbenes are used with alkynes as the starting reagents for the <a href="/wiki/Wulff%E2%80%93D%C3%B6tz_reaction" title="Wulff–Dötz reaction">Wulff–Dötz reaction</a>, forming phenols.<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> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Wulff%E2%80%93D%C3%B6tz_reaction_to_a_chromium_half-sandwich_complex.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Wulff%E2%80%93D%C3%B6tz_reaction_to_a_chromium_half-sandwich_complex.png/531px-Wulff%E2%80%93D%C3%B6tz_reaction_to_a_chromium_half-sandwich_complex.png" decoding="async" width="531" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Wulff%E2%80%93D%C3%B6tz_reaction_to_a_chromium_half-sandwich_complex.png/797px-Wulff%E2%80%93D%C3%B6tz_reaction_to_a_chromium_half-sandwich_complex.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Wulff%E2%80%93D%C3%B6tz_reaction_to_a_chromium_half-sandwich_complex.png/1062px-Wulff%E2%80%93D%C3%B6tz_reaction_to_a_chromium_half-sandwich_complex.png 2x" data-file-width="1932" data-file-height="316" /></a><figcaption>General reaction scheme for the Wullf-Dötz reaction, making phenols from Fisher carbene complexes and alkynes.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=10" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Chugaev%27s_Carbene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Chugaev%27s_Carbene.svg/392px-Chugaev%27s_Carbene.svg.png" decoding="async" width="392" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Chugaev%27s_Carbene.svg/588px-Chugaev%27s_Carbene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Chugaev%27s_Carbene.svg/784px-Chugaev%27s_Carbene.svg.png 2x" data-file-width="4956" data-file-height="1470" /></a><figcaption>The first metal carbene complex, <a href="/wiki/Lev_Aleksandrovich_Chugaev" class="mw-redirect" title="Lev Aleksandrovich Chugaev">Chugaev's red salt</a>, was not recognized as such until decades after its preparation.<sup id="cite_ref-:0_21-0" class="reference"><a href="#cite_note-:0-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>The first metal carbene complex to have been reported was <a href="/wiki/Lev_Chugaev#Contributions_to_coordination_chemistry" title="Lev Chugaev">Chugaev's red salt</a>, first synthesized as early as 1925, although it was never identified to be a carbene complex.<sup id="cite_ref-:0_21-1" class="reference"><a href="#cite_note-:0-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The characterization of (CO)5W(COCH3(Ph)) in the 1960s is often cited as the starting point of the area and <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Ernst Otto Fischer</a>, for this and other achievements in organometallic chemistry, was awarded the 1973 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a>.<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> In 1968, <a href="/wiki/Hans-Werner_Wanzlick" title="Hans-Werner Wanzlick">Hans-Werner Wanzlick</a> and Karl Öfele separately reported metal-bonded N-heterocyclic carbenes.<sup id="cite_ref-:1_6-6" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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><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> The synthesis and characterization of ((CH<sub>3</sub>)<sub>3</sub>CCH<sub>2</sub>)Ta=CHC(CH<sub>3</sub>)<sub>3</sub> by <a href="/wiki/Richard_R._Schrock" title="Richard R. Schrock">Richard R. Schrock</a> in 1974 marked the first metal alkylidene complex.<sup id="cite_ref-:2_9-1" class="reference"><a href="#cite_note-:2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In 1991, Anthony J. Arduengo synthesized and crystallized the first <a href="/wiki/Persistent_carbene" title="Persistent carbene">persistent carbene</a>, an NHC with large <a href="/wiki/Adamantane" title="Adamantane">adamantane</a> alkyl groups, accelerating the field of N-heterocarbene ligands to its current use.<sup id="cite_ref-arduengo2_5-1" class="reference"><a href="#cite_note-arduengo2-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_6-7" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=11" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Carbene_radical" title="Carbene radical">Carbene radical</a></li> <li><a href="/wiki/Carbyne" title="Carbyne">Carbyne</a></li> <li><a href="/wiki/Transition_metal_carbyne_complex" title="Transition metal carbyne complex">Transition metal carbyne complex</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_carbene_complex&action=edit&section=12" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-:3-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:3_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:3_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:3_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:3_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-:3_1-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFElschenbroichElschenbroich2011" class="citation book cs1">Elschenbroich, Christoph; Elschenbroich, Christoph (2011). <i>Organometallics</i> (3, compl. rev. and extended ed.). 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Ekkehardt; Jahnke, Mareike C. (2008-04-14). <a rel="nofollow" class="external text" href="https://onlinelibrary.wiley.com/doi/10.1002/anie.200703883">"Heterocyclic Carbenes: Synthesis and Coordination Chemistry"</a>. <i>Angewandte Chemie International Edition</i>. <b>47</b> (17): <span class="nowrap">3122–</span>3172. <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.200703883">10.1002/anie.200703883</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1433-7851">1433-7851</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18398856">18398856</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition&rft.atitle=Heterocyclic+Carbenes%3A+Synthesis+and+Coordination+Chemistry&rft.volume=47&rft.issue=17&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3122-%3C%2Fspan%3E3172&rft.date=2008-04-14&rft.issn=1433-7851&rft_id=info%3Apmid%2F18398856&rft_id=info%3Adoi%2F10.1002%2Fanie.200703883&rft.aulast=Hahn&rft.aufirst=F.+Ekkehardt&rft.au=Jahnke%2C+Mareike+C.&rft_id=https%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2F10.1002%2Fanie.200703883&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+carbene+complex" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFischerMaasböl1964" class="citation journal cs1">Fischer, E. O.; Maasböl, A. (August 1964). <a rel="nofollow" class="external text" href="https://onlinelibrary.wiley.com/doi/10.1002/anie.196405801">"On the Existence of a Tungsten Carbonyl Carbene Complex"</a>. <i>Angewandte Chemie International Edition in English</i>. <b>3</b> (8): <span class="nowrap">580–</span>581. <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.196405801">10.1002/anie.196405801</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0570-0833">0570-0833</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=On+the+Existence+of+a+Tungsten+Carbonyl+Carbene+Complex&rft.volume=3&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E580-%3C%2Fspan%3E581&rft.date=1964-08&rft_id=info%3Adoi%2F10.1002%2Fanie.196405801&rft.issn=0570-0833&rft.aulast=Fischer&rft.aufirst=E.+O.&rft.au=Maasb%C3%B6l%2C+A.&rft_id=https%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2F10.1002%2Fanie.196405801&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+carbene+complex" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWanzlickSchönherr1968" class="citation journal cs1">Wanzlick, H.-W.; Schönherr, H.-J. (February 1968). <a rel="nofollow" class="external text" href="https://onlinelibrary.wiley.com/doi/10.1002/anie.196801412">"Direct Synthesis of a Mercury Salt-Carbene Complex"</a>. <i>Angewandte Chemie International Edition in English</i>. <b>7</b> (2): <span class="nowrap">141–</span>142. <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.196801412">10.1002/anie.196801412</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0570-0833">0570-0833</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=Direct+Synthesis+of+a+Mercury+Salt-Carbene+Complex&rft.volume=7&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E141-%3C%2Fspan%3E142&rft.date=1968-02&rft_id=info%3Adoi%2F10.1002%2Fanie.196801412&rft.issn=0570-0833&rft.aulast=Wanzlick&rft.aufirst=H.-W.&rft.au=Sch%C3%B6nherr%2C+H.-J.&rft_id=https%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2F10.1002%2Fanie.196801412&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+carbene+complex" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFÖfele1968" class="citation journal cs1">Öfele, K. (June 1968). <a rel="nofollow" class="external text" href="https://doi.org/10.1016/S0022-328X(00)88691-X">"1,3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer übergangsmetall-carben-komplex"</a>. <i>Journal of Organometallic Chemistry</i>. <b>12</b> (3): <span class="nowrap">P42 –</span> <span class="nowrap">P43</span>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0022-328x%2800%2988691-x">10.1016/s0022-328x(00)88691-x</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-328X">0022-328X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Organometallic+Chemistry&rft.atitle=1%2C3-Dimethyl-4-imidazolinyliden-%282%29-pentacarbonylchrom+ein+neuer+%C3%BCbergangsmetall-carben-komplex&rft.volume=12&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3EP42+-%3C%2Fspan%3E+%3Cspan+class%3D%22nowrap%22%3EP43%3C%2Fspan%3E&rft.date=1968-06&rft_id=info%3Adoi%2F10.1016%2Fs0022-328x%2800%2988691-x&rft.issn=0022-328X&rft.aulast=%C3%96fele&rft.aufirst=K.&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%2FS0022-328X%2800%2988691-X&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+carbene+complex" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist 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href="/wiki/Template:Organometallics" title="Template:Organometallics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Organometallics" title="Template talk:Organometallics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Organometallics" title="Special:EditPage/Template:Organometallics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Organometallic_chemistry378" style="font-size:114%;margin:0 4em"><a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">Organometallic chemistry</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Principles</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Crystal_field_theory" title="Crystal field theory">Crystal field theory</a></li> <li><a href="/wiki/Ligand_field_theory" title="Ligand field theory">Ligand field theory</a></li> <li><a href="/wiki/18-electron_rule" title="18-electron rule">18-electron rule</a></li> <li><a href="/wiki/D_electron_count" title="D electron count">d electron count</a></li> <li><a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></li> <li><a href="/wiki/Isolobal_principle" title="Isolobal principle">Isolobal principle</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">π backbonding</a></li> <li><a href="/wiki/Dewar%E2%80%93Chatt%E2%80%93Duncanson_model" title="Dewar–Chatt–Duncanson model">Dewar–Chatt–Duncanson model</a></li> <li><a href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Spin_states_(d_electrons)" title="Spin states (d electrons)">spin states</a></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic interaction</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oxidative_addition" title="Oxidative addition">Oxidative addition</a> / <a href="/wiki/Reductive_elimination" title="Reductive elimination">reductive elimination</a></li> <li><a href="/wiki/Migratory_insertion" title="Migratory insertion">Migratory insertion</a></li> <li><a href="/wiki/Beta-Hydride_elimination" class="mw-redirect" title="Beta-Hydride elimination">β-hydride elimination</a></li> <li><a href="/wiki/Transmetalation" title="Transmetalation">Transmetalation</a></li> <li><a href="/wiki/Carbometalation" title="Carbometalation">Carbometalation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types of compounds</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gilman_reagent" title="Gilman reagent">Gilman reagents</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a></li> <li><a href="/wiki/Cyclopentadienyl_complex" title="Cyclopentadienyl complex">Cyclopentadienyl complexes</a></li> <li><a href="/wiki/Transition_metal_indenyl_complex" title="Transition metal indenyl complex">Transition metal indenyl complexes</a></li> <li><a href="/wiki/Transition_metal_fullerene_complex" title="Transition metal fullerene complex">Transition metal fullerene complexes</a></li> <li><a href="/wiki/Metallocene" title="Metallocene">Metallocenes</a></li> <li><a href="/wiki/Metal_tetranorbornyl" title="Metal tetranorbornyl">Metal tetranorbornyls</a></li> <li><a href="/wiki/Sandwich_compound" title="Sandwich compound">Sandwich compounds</a></li> <li><a href="/wiki/Half_sandwich_compound" title="Half sandwich compound">Half sandwich compounds</a></li> <li><a href="/wiki/Transition_metal_acyl_complexes" title="Transition metal acyl complexes">Transition metal acyl complexes</a></li> <li><a class="mw-selflink selflink">Transition metal carbene complexes</a></li> <li><a href="/wiki/Transition_metal_carbyne_complex" title="Transition metal carbyne complex">Transition metal carbyne complexes</a></li> <li><a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">Transition metal alkene complexes</a></li> <li><a href="/wiki/Transition_metal_alkyne_complex" title="Transition metal alkyne complex">Transition metal alkyne complexes</a></li> <li><a href="/wiki/Transition-metal_allyl_complex" title="Transition-metal allyl complex">Transition-metal allyl complexes</a></li> <li><a href="/wiki/Metal_carbido_complex" title="Metal carbido complex">Transition metal carbides</a></li> <li><a href="/wiki/Arene_complexes_of_univalent_gallium,_indium,_and_thallium" title="Arene complexes of univalent gallium, indium, and thallium">Arene complexes of univalent gallium, indium, and thallium</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Applications</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carbonylation" title="Carbonylation">Carbonylation</a></li> <li><a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a></li> <li><a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reaction</a></li> <li><a href="/wiki/Monsanto_process" title="Monsanto process">Monsanto process</a></li> <li><a href="/wiki/Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a></li> <li><a href="/wiki/Shell_higher_olefin_process" title="Shell higher olefin process">Shell higher olefin process</a></li> <li><a href="/wiki/Ziegler%E2%80%93Natta_catalyst" title="Ziegler–Natta catalyst">Ziegler–Natta process</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related branches of <a href="/wiki/Chemistry" title="Chemistry">chemistry</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic chemistry</a></li> <li><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Organometallic_chemistry" title="Category:Organometallic chemistry">Category</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <b><a href="https://commons.wikimedia.org/wiki/Category:Organometallic_chemistry" class="extiw" title="commons:Category:Organometallic chemistry">Commons</a></b></li></ul> </div></td></tr></tbody></table></div><div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Coordination_complexes113" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Coordination_complexes" title="Template:Coordination complexes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Coordination_complexes" title="Template talk:Coordination complexes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Coordination_complexes" title="Special:EditPage/Template:Coordination complexes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Coordination_complexes113" style="font-size:114%;margin:0 4em"><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination complexes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">H donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_hydride" title="Transition metal hydride">H<sup>−</sup></a></li> <li><a href="/wiki/Dihydrogen_complex" title="Dihydrogen complex">H<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">B donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_boryl_complex" title="Transition metal boryl complex">BR<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Metallaborane" title="Metallaborane">B<sub>m</sub>H<sub>n</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_alkyl_complexes" title="Transition metal alkyl complexes">R<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_acyl_complexes" title="Transition metal acyl complexes">RC(O)<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_formyl_complex" title="Transition metal formyl complex">HC(O)<sup>−</sup></a></li> <li><a href="/wiki/Transition-metal_allyl_complex" title="Transition-metal allyl complex">CH<sub>2</sub>＝CH-CH<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Trimethylenemethane_complexes" title="Trimethylenemethane complexes">C(CH<sub>2</sub>)<sub>3</sub></a></li> <li><a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">CH<sub>2</sub>＝CH<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_alkyne_complex" title="Transition metal alkyne complex">RC<sub>2</sub>R</a></li> <li><a href="/wiki/Transition_metal_benzyne_complex" title="Transition metal benzyne complex">C<sub>6</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Cyanometalate" title="Cyanometalate">CN<sup>−</sup></a></li> <li><a href="/wiki/Metal_carbonyl" title="Metal carbonyl">CO</a></li> <li><a href="/wiki/Metal_carbon_dioxide_complex" title="Metal carbon dioxide complex">CO<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_carbide" class="mw-redirect" title="Transition metal carbide">C<sup>4-</sup></a></li> <li><a href="/wiki/Transition_metal_arene_complex" title="Transition metal arene complex">C<sub>6</sub>R<sub>6</sub></a></li> <li><a href="/wiki/Transition_metal_fullerene_complex" title="Transition metal fullerene complex">C<sub>60</sub> & C<sub>70</sub></a></li> <li><a href="/wiki/Transition_metal_isocyanide_complexes" title="Transition metal isocyanide complexes">RNC</a></li> <li><a class="mw-selflink selflink">=CR<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_carbyne_complex" title="Transition metal carbyne complex">≡CR</a></li> <li><a href="/wiki/Metallocene" title="Metallocene">C<sub>5</sub>H<sub>5</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_indenyl_complex" title="Transition metal indenyl complex">C<sub>9</sub>H<sub>7</sub><sup>−</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Si donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_silane_complexes" class="mw-redirect" title="Transition metal silane complexes">H<sub>n</sub>SiR<sub>4−n</sub></a></li> <li><a href="/wiki/Transition_metal_silyl_complexes" title="Transition metal silyl complexes">R<sub>3</sub>Si<sup>−</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">N donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metal_ammine_complex" title="Metal ammine complex">NH<sub>3</sub></a></li> <li><a href="/wiki/Transition_metal_azide_complex" title="Transition metal azide complex">N<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_imidazole_complex" title="Transition metal imidazole complex">imidazole</a></li> <li><a href="/wiki/Metal_nitrosyl_complex" title="Metal nitrosyl complex">NO</a></li> <li><a href="/wiki/Transition_metal_nitroso_complexes" title="Transition metal nitroso complexes">RNO</a></li> <li><a href="/wiki/Transition_metal_nitrite_complex#Bonding_modes" title="Transition metal nitrite complex">NO<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_pyridine_complexes" title="Transition metal pyridine complexes">py</a></li> <li><a href="/wiki/Transition_metal_amino_acid_complexes" title="Transition metal amino acid complexes">amino acid</a></li> <li><a href="/wiki/Metal_nitrido_complex" title="Metal nitrido complex">N<sup>3-</sup></a></li> <li><a href="/wiki/Transition_metal_imido_complex" title="Transition metal imido complex">RN<sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_nitrile_complexes" title="Transition metal nitrile complexes">RCN</a></li> <li><a href="/wiki/Transition_metal_complexes_of_2,2%27-bipyridine" title="Transition metal complexes of 2,2'-bipyridine">bipy</a></li> <li><a href="/wiki/Transition_metal_complexes_of_1,10-phenanthroline" title="Transition metal complexes of 1,10-phenanthroline">phen</a></li> <li><a href="/wiki/Transition_metal_porphyrin_complexes" title="Transition metal porphyrin complexes">porphyrin</a></li> <li><a href="/wiki/Metal_bis(trimethylsilyl)amides" title="Metal bis(trimethylsilyl)amides">(Me<sub>3</sub>Si)<sub>2</sub>N<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_dinitrogen_complex" title="Transition metal dinitrogen complex">N<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_complexes_of_thiocyanate" title="Transition metal complexes of thiocyanate"><i>N</i>CS<sup>−</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">P donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metal_phosphine_complex" class="mw-redirect" title="Metal phosphine complex">PR<sub>3</sub></a></li> <li><a href="/wiki/Transition_metal_phosphido_complexes" title="Transition metal phosphido complexes">PR<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_complexes_of_phosphine_oxides#Secondary_phosphine_oxides_as_ligands" title="Transition metal complexes of phosphine oxides">PR<sub>2</sub>OH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">O donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metal_aquo_complex" title="Metal aquo complex">H<sub>2</sub>O</a></li> <li><a href="/wiki/Transition_metal_hydroxide_complexes" title="Transition metal hydroxide complexes">OH<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_ether_complex" title="Transition metal ether complex">R<sub>2</sub>O</a></li> <li><a href="/wiki/Metal_alkoxide" class="mw-redirect" title="Metal alkoxide">RO<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_oxo_complex" title="Transition metal oxo complex">O<sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_dioxygen_complex" title="Transition metal dioxygen complex">O<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_carbonate_and_bicarbonate_complexes" title="Transition metal carbonate and bicarbonate complexes">CO<sub>3</sub><sup>2-</sup>/HCO<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_oxalate_complex" title="Transition metal oxalate complex">C<sub>2</sub>O<sub>4</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_carboxylate_complex" title="Transition metal carboxylate complex">RCO<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Metal_acetylacetonates" title="Metal acetylacetonates">acac</a></li> <li><a href="/wiki/Transition_metal_complexes_of_aldehydes_and_ketones" title="Transition metal complexes of aldehydes and ketones">R<sub>2</sub>CO</a></li> <li><a href="/wiki/Transition_metal_nitrite_complex" title="Transition metal nitrite complex">ONO<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_nitrate_complex" title="Transition metal nitrate complex">NO<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_perchlorate_complexes" title="Transition metal perchlorate complexes">ClO<sub>4</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_complexes_of_pyridine-N-oxides" title="Transition metal complexes of pyridine-N-oxides">C<sub>5</sub>H<sub>5</sub>NO</a></li> <li><a href="/wiki/Transition_metal_sulfoxide_complex" title="Transition metal sulfoxide complex">OSR<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_sulfate_complex" title="Transition metal sulfate complex">SO<sub>4</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_phosphate_complex" title="Transition metal phosphate complex">PO<sub>4</sub><sup>3-</sup></a></li> <li><a href="/wiki/Transition_metal_complexes_of_phosphine_oxides" title="Transition metal complexes of phosphine oxides">OPR<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">S donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_dithiocarbamate_complexes" title="Transition metal dithiocarbamate complexes">R<sub>2</sub>NCS<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_thiolate_complex" title="Transition metal thiolate complex">RS<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_thioether_complex" title="Transition metal thioether complex">R<sub>2</sub>S</a></li> <li><a href="/wiki/Metal_dithiolene_complex" title="Metal dithiolene complex">R<sub>2</sub>C<sub>2</sub>S<sub>2</sub><sup>2-</sup></a></li> <li><a href="/wiki/Metal_sulfur_dioxide_complex" title="Metal sulfur dioxide complex">SO<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_sulfito_complex" title="Transition metal sulfito complex">SO<sub>3</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_thiosulfate_complex" title="Transition metal thiosulfate complex">S<sub>2</sub>O<sub>3</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_sulfoxide_complex" title="Transition metal sulfoxide complex">SR<sub>2</sub>O</a></li> <li><a href="/wiki/Transition_metal_complexes_of_thiocyanate" title="Transition metal complexes of thiocyanate">NC<i>S</i><sup>−</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Halide donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Fluoro_complex&action=edit&redlink=1" class="new" title="Fluoro complex (page does not exist)">F<sup>−</sup></a></li> <li><a href="/wiki/Difluorine_complex" title="Difluorine complex">F<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_chloride_complex" title="Transition metal chloride complex">Cl<sup>−</sup></a></li> <li><a href="/w/index.php?title=Bromo_complex&action=edit&redlink=1" class="new" title="Bromo complex (page does not exist)">Br<sup>−</sup></a></li> <li><a href="/w/index.php?title=Iodo_complex&action=edit&redlink=1" class="new" title="Iodo complex (page does not exist)">I<sup>−</sup></a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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