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<li id="toc-Half-sandwich_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Half-sandwich_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Half-sandwich compounds</span> </div> </a> <ul id="toc-Half-sandwich_compounds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Multidecker_sandwiches" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Multidecker_sandwiches"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Multidecker sandwiches</span> </div> </a> <ul id="toc-Multidecker_sandwiches-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Linked_sandwiches" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Linked_sandwiches"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Linked sandwiches</span> </div> </a> <ul id="toc-Linked_sandwiches-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Inverse_sandwiches" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Inverse_sandwiches"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Inverse sandwiches</span> </div> </a> <ul id="toc-Inverse_sandwiches-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Double-_and_multimetallic_sandwich_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Double-_and_multimetallic_sandwich_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5</span> <span>Double- and multimetallic sandwich compounds</span> </div> </a> <ul id="toc-Double-_and_multimetallic_sandwich_compounds-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span 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href="https://cs.wikipedia.org/wiki/Sendvi%C4%8Dov%C3%A9_slou%C4%8Deniny" title="Sendvičové sloučeniny – Czech" lang="cs" hreflang="cs" data-title="Sendvičové sloučeniny" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Sandwichkomplexe" title="Sandwichkomplexe – German" lang="de" hreflang="de" data-title="Sandwichkomplexe" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Compuesto_s%C3%A1ndwich" title="Compuesto sándwich – Spanish" lang="es" hreflang="es" data-title="Compuesto sándwich" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%B1%DA%A9%DB%8C%D8%A8_%D8%B3%D8%A7%D9%86%D8%AF%D9%88%DB%8C%DA%86%DB%8C" title="ترکیب ساندویچی – Persian" lang="fa" hreflang="fa" data-title="ترکیب ساندویچی" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Compos%C3%A9_sandwich" title="Composé sandwich – French" lang="fr" hreflang="fr" data-title="Composé sandwich" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%83%8C%EB%93%9C%EC%9C%84%EC%B9%98_%ED%99%94%ED%95%A9%EB%AC%BC" title="샌드위치 화합물 – Korean" lang="ko" hreflang="ko" data-title="샌드위치 화합물" data-language-autonym="한국어" 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sandwich – Romanian" lang="ro" hreflang="ro" data-title="Compus sandwich" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Sandvi%C3%A7_bile%C5%9Fik" title="Sandviç bileşik – Turkish" lang="tr" hreflang="tr" data-title="Sandviç bileşik" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D0%B5%D0%BD%D0%B4%D0%B2%D1%96%D1%87%D0%BD%D0%B0_%D1%81%D0%BF%D0%BE%D0%BB%D1%83%D0%BA%D0%B0" title="Сендвічна сполука – Ukrainian" lang="uk" hreflang="uk" data-title="Сендвічна сполука" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link 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.mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Primary_sources plainlinks metadata ambox ambox-content ambox-Primary_sources" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>relies excessively on <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">references</a> to <a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research">primary sources</a></b>.<span class="hide-when-compact"> Please improve this article by adding <a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research">secondary or tertiary sources</a>. <br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Sandwich+compound%22">"Sandwich compound"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Sandwich+compound%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Sandwich+compound%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Sandwich+compound%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Sandwich+compound%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Sandwich+compound%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">March 2017</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ferrocene_3d_model_2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Ferrocene_3d_model_2.png/220px-Ferrocene_3d_model_2.png" decoding="async" width="220" height="196" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Ferrocene_3d_model_2.png/330px-Ferrocene_3d_model_2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/Ferrocene_3d_model_2.png/440px-Ferrocene_3d_model_2.png 2x" data-file-width="1088" data-file-height="968" /></a><figcaption>Space-filling model of <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a>, the archetypal sandwich compound</figcaption></figure> <p>In <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>, a <b>sandwich compound</b> is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> featuring a <a href="/wiki/Metal" title="Metal">metal</a> bound by <a href="/wiki/Hapticity" title="Hapticity">haptic</a>, <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bonds</a> to two <a href="/wiki/Arene_compound" class="mw-redirect" title="Arene compound">arene</a> (ring) <a href="/wiki/Ligand" title="Ligand">ligands</a>. The arenes have the formula <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">C<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub"><i>n</i></sub></span>, substituted derivatives (for example <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub"><i>n</i></sub>(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub"><i>n</i></sub></span>) and <a href="/wiki/Heterocycle" class="mw-redirect" title="Heterocycle">heterocyclic</a> derivatives (for example <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">BC<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub"><i>n</i>+1</sub></span>). Because the metal is usually situated between the two rings, it is said to be "sandwiched". A special class of sandwich complexes are the <a href="/wiki/Metallocenes" class="mw-redirect" title="Metallocenes">metallocenes</a>. </p><p>The term <i>sandwich compound</i> was introduced in organometallic nomenclature in 1956 in a report by J. D. Dunitz, L. E. Orgel and R. A. Rich, who confirmed the structure of <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a> by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The correct structure, in which the molecule features an iron atom <i>sandwiched</i> between two parallel <a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a> rings, had been proposed several years previously by <a href="/wiki/Robert_Burns_Woodward" title="Robert Burns Woodward">Robert Burns Woodward</a> and, separately, by <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Ernst Otto Fischer</a>. The structure helped explain puzzles about ferrocene's <a href="/wiki/Conformational_isomerism" title="Conformational isomerism">conformers</a>. This result further demonstrated the power of <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> and accelerated the growth of <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (October 2019)">page needed</span></a></i>]</sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Classes">Classes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sandwich_compound&action=edit&section=1" title="Edit section: Classes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Troticene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Troticene.svg/122px-Troticene.svg.png" decoding="async" width="122" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Troticene.svg/183px-Troticene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Troticene.svg/244px-Troticene.svg.png 2x" data-file-width="77" data-file-height="75" /></a><figcaption><a href="/wiki/(Cycloheptatrienyl)(cyclopentadienyl)titanium" title="(Cycloheptatrienyl)(cyclopentadienyl)titanium">(Cycloheptatrienyl)(cyclopentadienyl)titanium</a> (troticene) is an unsymmetrical sandwich complex.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </figcaption></figure></dd></dl> <p>The best known members are the <a href="/wiki/Metallocene" title="Metallocene">metallocenes</a> of the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">M(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub></span> where M = <a href="/wiki/Chromocene" title="Chromocene">Cr</a>, <a href="/wiki/Ferrocene" title="Ferrocene">Fe</a>, <a href="/wiki/Cobaltocene" title="Cobaltocene">Co</a>, <a href="/wiki/Nickelocene" title="Nickelocene">Ni</a>, <a href="/wiki/Plumbocene" title="Plumbocene">Pb</a>, <a href="/wiki/Zirconocene_dichloride" title="Zirconocene dichloride">Zr</a>, <a href="/wiki/Ruthenocene" title="Ruthenocene">Ru</a>, <a href="/wiki/Rhodocene" title="Rhodocene">Rh</a>, <a href="/wiki/Osmocene" title="Osmocene">Os</a>, <a href="/wiki/Samarium#Organometallic_compounds" title="Samarium">Sm</a>, <a href="/wiki/Titanocene_dichloride" title="Titanocene dichloride">Ti</a>, <a href="/wiki/Vanadocene_dichloride" title="Vanadocene dichloride">V</a>, <a href="/wiki/Molybdocene_dichloride" title="Molybdocene dichloride">Mo</a>, W, Zn. These species are also called bis(cyclopentadienyl)metal complexes. Other arenes can serve as ligands as well. </p> <ul><li>Mixed cyclopentadienyl complexes: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">M(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)(C<sub><i>n</i></sub>H<sub><i>n</i></sub>)</span>. Some examples are <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ti(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)(C<sub class="template-chem2-sub">7</sub>H<sub class="template-chem2-sub">7</sub>) and (C<sub><sub class="template-chem2-sub">60</sub></sub>)Fe(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>Ph<sub class="template-chem2-sub">5</sub>)</span> where the <a href="/wiki/Fullerene_Ligands" class="mw-redirect" title="Fullerene Ligands">fullerene ligand</a> is acting as a cyclopentadienyl analogue.</li> <li>Bis(benzene) complexes: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">M(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub>)<sub class="template-chem2-sub">2</sub></span>, the best known example being <a href="/wiki/Bis(benzene)chromium" title="Bis(benzene)chromium">bis(benzene)chromium</a>.</li> <li>Bis(cyclooctatetraenyl) complexes: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">M(C<sub class="template-chem2-sub">8</sub>H<sub class="template-chem2-sub">8</sub>)<sub class="template-chem2-sub">2</sub></span>, such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Uranocene" title="Uranocene">U(C<sub class="template-chem2-sub">8</sub>H<sub class="template-chem2-sub">8</sub>)<sub class="template-chem2-sub">2</sub></a></span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Th(C<sub class="template-chem2-sub">8</sub>H<sub class="template-chem2-sub">8</sub>)<sub class="template-chem2-sub">2</sub></span> (both <a href="/wiki/Actinocene" title="Actinocene">actinocenes</a>).</li> <li>Metal–<a href="/wiki/Carborane" title="Carborane">carborane</a> complexes (metallacarboranes), a very large and diverse family in which main-group or transition metal ions are coordinated to carborane ligands to form <a href="/wiki/Cage_compound" class="mw-redirect" title="Cage compound">polyhedral cages</a> ranging in size from 6 to 15 vertices. Examples include bis(<a href="/wiki/Dicarbollide" title="Dicarbollide">dicarbollide</a>) complexes,<sup id="cite_ref-kang1991_4-0" class="reference"><a href="#cite_note-kang1991-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[M(C<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">9</sub>H<sub class="template-chem2-sub">11</sub>)<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup"><i>z</i>−</sup></span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Fe(C<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">9</sub>H<sub class="template-chem2-sub">11</sub>)<sub class="template-chem2-sub">2</sub>]<sup>2−</sup></span>, and small-carborane sandwiches such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(R<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>)M(C<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">6</sub>)</span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(R<sub class="template-chem2-sub">5</sub>C<sub class="template-chem2-sub">5</sub>)M(R′<sub class="template-chem2-sub">2</sub>)C<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">4</sub>)</span> where M is a transition metal and R and R′ are methyl or ethyl.<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><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></li></ul> <p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Small_carborane_sandwiches.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/b/b4/Small_carborane_sandwiches.png" decoding="async" width="631" height="209" class="mw-file-element" data-file-width="631" data-file-height="209" /></a></span> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:KIWJOP.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/KIWJOP.png/220px-KIWJOP.png" decoding="async" width="220" height="334" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/KIWJOP.png/330px-KIWJOP.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/KIWJOP.png/440px-KIWJOP.png 2x" data-file-width="1200" data-file-height="1820" /></a><figcaption>Structure of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(Me<sub class="template-chem2-sub">4</sub>N<sup class="template-chem2-sup">+</sup>)<sub class="template-chem2-sub">2</sub>[Fe(C<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">9</sub>H<sub class="template-chem2-sub">11</sub>)<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">+</sup></span>, showing only one <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Tetramethylammonium" title="Tetramethylammonium">Me<sub class="template-chem2-sub">4</sub>N<sup class="template-chem2-sup">+</sup></a></span>.<sup id="cite_ref-kang1991_4-1" class="reference"><a href="#cite_note-kang1991-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Closely related are the metal complexes containing <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>C<sub class="template-chem2-sub">3</sub>B<sub class="template-chem2-sub">2</sub>R<sub class="template-chem2-sub">2</sub></span> (<a href="/w/index.php?title=Diborolyl&action=edit&redlink=1" class="new" title="Diborolyl (page does not exist)">diborolyl</a>) ligands.<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> In addition to these, other sandwich complexes containing purely inorganic ligands are known, such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Fe(C<sub class="template-chem2-sub">5</sub>Me<sub class="template-chem2-sub">5</sub>)(P<sub class="template-chem2-sub">5</sub>)</span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[(P<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>Ti]<sup>2−</sup></span>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Half-sandwich_compounds">Half-sandwich compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sandwich_compound&action=edit&section=2" title="Edit section: Half-sandwich compounds"><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/Half-sandwich_compound" class="mw-redirect" title="Half-sandwich compound">Half-sandwich compound</a></div> <p>Half sandwich complexes have only one facially-bound planar organic <a href="/wiki/Ligand" title="Ligand">ligand</a> instead of two gives rise to a still larger family of <b>half-sandwich</b> compounds. One well studied example is probably <a href="/wiki/Methylcyclopentadienyl_manganese_tricarbonyl" title="Methylcyclopentadienyl manganese tricarbonyl">methylcyclopentadienyl manganese tricarbonyl</a>. Such species are occasionally referred to as <b>piano-stool compounds</b>, at least when there are three diatomic ligands. In such cases, the facially-bound planar organic ligand comprises the "seat" of the piano stool. </p> <div class="mw-heading mw-heading3"><h3 id="Multidecker_sandwiches">Multidecker sandwiches</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sandwich_compound&action=edit&section=3" title="Edit section: Multidecker sandwiches"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first isolated multidecker sandwich was the tris(<a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a>)di<a href="/wiki/Nickel" title="Nickel">nickel</a> triple-decker complex <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Ni<sub class="template-chem2-sub">2</sub>Cp<sub class="template-chem2-sub">3</sub>]<a href="/wiki/Tetrafluoroborate" title="Tetrafluoroborate">BF<sub class="template-chem2-sub">4</sub></a></span>, a highly air- and water-sensitive compound reported in 1972,<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> with X-ray crystallographic confirmation in 1974.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>In 1973 the electrically neutral air-stable triple-decker cobaltacarborane sandwiches 1,7,2,3- and 1,7,2,4-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CpCo(RHC<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">3</sub>)Cp</span> (where R = H, Me) were isolated and characterized by multinuclear <a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">NMR</a> and <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray</a> studies<sup id="cite_ref-grimes1974_11-0" class="reference"><a href="#cite_note-grimes1974-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> (the structure of the 1,7,2,3 isomer is shown). </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Co2C2B3_triple-decker1.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Co2C2B3_triple-decker1.jpg/220px-Co2C2B3_triple-decker1.jpg" decoding="async" width="220" height="307" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Co2C2B3_triple-decker1.jpg/330px-Co2C2B3_triple-decker1.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/9/94/Co2C2B3_triple-decker1.jpg 2x" data-file-width="376" data-file-height="525" /></a><figcaption>1,7,2,3-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CpCo(MeC<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">4</sub>)CoCp</span>, the first structurally confirmed multidecker sandwich.<sup id="cite_ref-grimes1974_11-1" class="reference"><a href="#cite_note-grimes1974-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Since then many three-, four-, five-, and six-decker sandwich complexes have been described.<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> The largest structurally characterized multidecker sandwich monomer is the hexadecker shown at lower right.<sup id="cite_ref-wang44_14-0" class="reference"><a href="#cite_note-wang44-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Hexadecker.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/4/44/Hexadecker.jpg" decoding="async" width="169" height="514" class="mw-file-element" data-file-width="169" data-file-height="514" /></a><figcaption>A structurally characterized cobaltacarborane hexadecker.<sup id="cite_ref-wang44_14-1" class="reference"><a href="#cite_note-wang44-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>An extensive family of multidecker sandwiches incorporating planar <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(R<sub class="template-chem2-sub">2</sub>R′C<sub class="template-chem2-sub">3</sub>B<sub class="template-chem2-sub">2</sub>R″<sub class="template-chem2-sub">2</sub>)<sup>3−</sup></span> (diborolyl) ligands has also been prepared.<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> </p><p>Numerous multidecker sandwich compounds featuring hydrocarbon bridging rings have also been prepared, especially triple deckers.<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> A versatile method involves the attachment of <a href="/wiki/Pentamethylcyclopentadiene" title="Pentamethylcyclopentadiene">Cp*</a>Ru<sup>+</sup> to preformed sandwich complexes.<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> <div class="mw-heading mw-heading3"><h3 id="Linked_sandwiches">Linked sandwiches</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sandwich_compound&action=edit&section=4" title="Edit section: Linked sandwiches"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Monomeric double-decker and multidecker sandwiches have been used as building blocks for extended systems, some of which exhibit electron delocalization between metal centers. An example of a cyclic poly(metallacarborane) complex is the octahedral "carbon-wired" system shown below, which contains a planar <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">16</sub>B<sub class="template-chem2-sub">8</sub></span> macrocycle.<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> </p><p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Carbon-wired_tetracobaltacarborane2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/2/2d/Carbon-wired_tetracobaltacarborane2.jpg" decoding="async" width="316" height="307" class="mw-file-element" data-file-width="316" data-file-height="307" /></a></span> </p> <div class="mw-heading mw-heading3"><h3 id="Inverse_sandwiches">Inverse sandwiches</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sandwich_compound&action=edit&section=5" title="Edit section: Inverse sandwiches"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In these <i>anti</i>-bimetallic compounds, the metals are found to be bridged by a single carbocyclic ring. Examples include <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[(THF)<sub class="template-chem2-sub">3</sub>Ca]<sub class="template-chem2-sub">2</sub>(<sub class="template-chem2-sub">1</sub>,<sub class="template-chem2-sub">3</sub>,<sub class="template-chem2-sub">5</sub>-triphenylbenzene)</span><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> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[(Ar)Sn]<sub class="template-chem2-sub">2</sub><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">COT</a></span>. </p> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:254px;max-width:254px"><div class="trow"><div class="tsingle" style="width:252px;max-width:252px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-vdW.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-vdW.png/250px-Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-vdW.png" decoding="async" width="250" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-vdW.png/375px-Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/23/Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-vdW.png/500px-Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-vdW.png 2x" data-file-width="1100" data-file-height="566" /></a></span></div></div></div><div class="trow"><div class="tsingle" style="width:252px;max-width:252px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-balls-B.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-balls-B.png/250px-Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-balls-B.png" decoding="async" width="250" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-balls-B.png/375px-Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-balls-B.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-balls-B.png/500px-Perylene-tetrapalladium-sandwich-complex-from-xtal-3D-balls-B.png 2x" data-file-width="1100" data-file-height="521" /></a></span></div></div></div><div class="trow"><div class="tsingle" style="width:252px;max-width:252px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:PeryleneTetrapalladiumSandwichComplex.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/PeryleneTetrapalladiumSandwichComplex.png/250px-PeryleneTetrapalladiumSandwichComplex.png" decoding="async" width="250" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/PeryleneTetrapalladiumSandwichComplex.png/375px-PeryleneTetrapalladiumSandwichComplex.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/PeryleneTetrapalladiumSandwichComplex.png/500px-PeryleneTetrapalladiumSandwichComplex.png 2x" data-file-width="1003" data-file-height="447" /></a></span></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">Perylene–tetrapalladium sandwich complex</div></div></div></div> <div class="mw-heading mw-heading3"><h3 id="Double-_and_multimetallic_sandwich_compounds">Double- and multimetallic sandwich compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sandwich_compound&action=edit&section=6" title="Edit section: Double- and multimetallic sandwich compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Another family of sandwich compound involves more than one metal sandwiched between two carbocyclic rings. Examples of the double sandwich include <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">V<sub class="template-chem2-sub">2</sub>(<a href="/wiki/Indene" title="Indene">indenyl</a>)<sub class="template-chem2-sub">2</sub></span>,<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> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ni<sub class="template-chem2-sub">2</sub>(<a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">COT</a>)<sub class="template-chem2-sub">2</sub></span><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> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cr<sub class="template-chem2-sub">2</sub>(pentalene)<sub class="template-chem2-sub">2</sub></span>. Depicted at right is an example of a multimetallic sandwich compound, which has four <a href="/wiki/Palladium" title="Palladium">palladium</a> atoms joined in a chain sandwiched between two <a href="/wiki/Perylene" title="Perylene">perylene</a> units.<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> The <a href="/wiki/Counterion" title="Counterion">counterions</a> are bulky <a href="/wiki/Noncoordinating_anion" class="mw-redirect" title="Noncoordinating anion">tetraarylborates</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sandwich_compound&action=edit&section=7" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ferrocene and <a href="/wiki/Methylcyclopentadienyl_manganese_tricarbonyl" title="Methylcyclopentadienyl manganese tricarbonyl">methylcyclopentadienyl manganese tricarbonyl</a> have been used as <a href="/wiki/Antiknock_agent" title="Antiknock agent">antiknock agents</a>. Certain bent metallocenes of zirconium and hafnium are effective precatalysts for the polymerization of <a href="/wiki/Propylene" title="Propylene">propylene</a>. Many half sandwich complexes of ruthenium, such as those derived from <a href="/wiki/(cymene)ruthenium_dichloride_dimer" class="mw-redirect" title="(cymene)ruthenium dichloride dimer">(cymene)ruthenium dichloride dimer</a> catalyse <a href="/wiki/Transfer_hydrogenation" title="Transfer hydrogenation">transfer hydrogenation</a>, a useful reaction in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>.<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 class="noprint Inline-Template noprint Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research"><span title="This claim needs references to reliable secondary sources. (December 2016)">non-primary source needed</span></a></i>]</sup> </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Metallocenes3.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/1/13/Metallocenes3.png" decoding="async" width="472" height="166" class="mw-file-element" data-file-width="472" data-file-height="166" /></a></span></dd></dl> <div style="clear:both;" class=""></div><p> Ferrocene derivatives have also been used as <a href="/wiki/Photoinitiator" title="Photoinitiator">photoinitiators</a> in <a href="/wiki/Cationic_polymerization" title="Cationic polymerization">cationic polymerization</a>.<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> </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=Sandwich_compound&action=edit&section=8" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</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="CITEREFDunitzOrgelRich1956" class="citation journal cs1">Dunitz, J.; Orgel, L.; Rich, A. (1956). <a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0365110X56001091">"The crystal structure of ferrocene"</a>. <i><a href="/wiki/Acta_Crystallographica" title="Acta Crystallographica">Acta Crystallographica</a></i>. <b>9</b> (4): 373–375. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0365110X56001091">10.1107/S0365110X56001091</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Crystallographica&rft.atitle=The+crystal+structure+of+ferrocene&rft.volume=9&rft.issue=4&rft.pages=373-375&rft.date=1956&rft_id=info%3Adoi%2F10.1107%2FS0365110X56001091&rft.aulast=Dunitz&rft.aufirst=J.&rft.au=Orgel%2C+L.&rft.au=Rich%2C+A.&rft_id=https%3A%2F%2Fdoi.org%2F10.1107%252FS0365110X56001091&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASandwich+compound" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMiesslerTarr2004" class="citation book cs1">Miessler, G. L.; Tarr, Donald A. (2004). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/inorganicchemist03edmies"><i>Inorganic Chemistry</i></a></span>. Upper Saddle River, NJ: Pearson Education. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-13-035471-6" title="Special:BookSources/0-13-035471-6"><bdi>0-13-035471-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Inorganic+Chemistry&rft.place=Upper+Saddle+River%2C+NJ&rft.pub=Pearson+Education&rft.date=2004&rft.isbn=0-13-035471-6&rft.aulast=Miessler&rft.aufirst=G.+L.&rft.au=Tarr%2C+Donald+A.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Finorganicchemist03edmies&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASandwich+compound" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZeinstraDe_Boer1973" class="citation journal cs1">Zeinstra, J.D.; De Boer, J.L. (1973). 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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 class="mw-selflink selflink">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 href="/wiki/Transition_metal_carbene_complex" title="Transition metal carbene complex">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 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