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href="https://azb.wikipedia.org/wiki/%D8%A2%DB%8C%DB%8C%D8%B1%D8%A7%DA%86_%D8%B4%D9%88%D8%A7%D8%B1%D8%AF%D8%B2" title="آییراچ شواردز – South Azerbaijani" lang="azb" hreflang="azb" data-title="آییراچ شواردز" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Schwartz-Reagenz" title="Schwartz-Reagenz – German" lang="de" hreflang="de" data-title="Schwartz-Reagenz" 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/Reactivo_de_Schwartz" title="Reactivo de Schwartz – Spanish" lang="es" hreflang="es" data-title="Reactivo de Schwartz" data-language-autonym="Español" data-language-local-name="Spanish" 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typeof="mw:File"><a href="/wiki/File:Cp4Zr2H2Cl2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Cp4Zr2H2Cl2.png/154px-Cp4Zr2H2Cl2.png" decoding="async" width="154" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Cp4Zr2H2Cl2.png/231px-Cp4Zr2H2Cl2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Cp4Zr2H2Cl2.png/308px-Cp4Zr2H2Cl2.png 2x" data-file-width="1574" data-file-height="961" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Schwartz%27s-reagent-dimer-from-xtal-3D-bs-17-ar.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Schwartz%27s-reagent-dimer-from-xtal-3D-bs-17-ar.png/150px-Schwartz%27s-reagent-dimer-from-xtal-3D-bs-17-ar.png" decoding="async" width="150" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Schwartz%27s-reagent-dimer-from-xtal-3D-bs-17-ar.png/225px-Schwartz%27s-reagent-dimer-from-xtal-3D-bs-17-ar.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Schwartz%27s-reagent-dimer-from-xtal-3D-bs-17-ar.png/300px-Schwartz%27s-reagent-dimer-from-xtal-3D-bs-17-ar.png 2x" data-file-width="2692" data-file-height="2000" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Chloridohydridozirconocene</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">chloridobis(η<sup>5</sup>-cyclopentadienyl)hydridozirconium</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Cp<sub>2</sub>ZrClH, zirconocene chloride hydride</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=37342-97-5">37342-97-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=%5BcH-%5D1cccc1.%5BcH-%5D1cccc1.Cl%5BZrH%2B2%5D">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.28605366.html">28605366</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.048.599">100.048.599</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q412819#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>253-479-5</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/53384630">53384630</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/S84D01XQGL">S84D01XQGL</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID30894914">DTXSID30894914</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q412819#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/2C5H5.ClH.Zr.H/c2*1-2-4-5-3-1;;;/h2*1-5H;1H;;/q2*-1;;+3;/p-1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: GBJQOFBMEJYDAU-UHFFFAOYSA-M</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/2C5H5.ClH.Zr.H/c2*1-2-4-5-3-1;;;/h2*1-5H;1H;;/q2*-1;;+3;/p-1/r2C5H5.ClHZr/c2*1-2-4-5-3-1;1-2/h2*1-5H;2H/q2*-1;+2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: GBJQOFBMEJYDAU-CFXPZLBWAB</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">[cH-]1cccc1.[cH-]1cccc1.Cl[ZrH+2]</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>10</sub>H<sub>11</sub>ClZr  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>257.87 g/mol    </td></tr> <tr> <td>Appearance </td> <td>White solid </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H228: Flammable solid">H228</abbr>, <abbr class="abbr" title="H261: In contact with water releases flammable gas">H261</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P231+P232: Handle and store contents under inert gas. Protect from moisture">P231+P232</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P402+P404: Store in a dry place. Store in a closed container.">P402+P404</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=401437383&page2=Schwartz%26%2339%3Bs+reagent">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Schwartz's reagent</b> is the common name for the <a href="/wiki/Organozirconium_compound" class="mw-redirect" title="Organozirconium compound">organozirconium compound</a> with the <a href="/wiki/Empirical_formula" title="Empirical formula">formula</a> (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl, sometimes called <b>zirconocene hydrochloride</b> or <b>zirconocene chloride hydride</b>, and is named after Jeffrey Schwartz, a chemistry professor at <a href="/wiki/Princeton_University" title="Princeton University">Princeton University</a>. This <a href="/wiki/Metallocene" title="Metallocene">metallocene</a> is used in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> for various transformations of <a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">alkenes</a> and <a href="/wiki/Alkynes" class="mw-redirect" title="Alkynes">alkynes</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Schwartz%27s_reagent&action=edit&section=1" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The complex was first prepared by Wailes and Weigold.<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> It can be purchased or readily prepared by reduction of <a href="/wiki/Zirconocene_dichloride" title="Zirconocene dichloride">zirconocene dichloride</a> with <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>: </p> <dl><dd>(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrCl<sub>2</sub> + <style data-mw-deduplicate="TemplateStyles:r1154941027">.mw-parser-output .frac{white-space:nowrap}.mw-parser-output .frac .num,.mw-parser-output .frac .den{font-size:80%;line-height:0;vertical-align:super}.mw-parser-output .frac .den{vertical-align:sub}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style><span class="frac"><span class="num">1</span>⁄<span class="den">4</span></span> LiAlH<sub>4</sub> → (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl + <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">4</span></span> <a href="/wiki/Lithium_tetrachloroaluminate" title="Lithium tetrachloroaluminate">LiAlCl<sub>4</sub></a></dd></dl> <p>This reaction also affords (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrH<sub>2</sub>, which is treated with <a href="/wiki/Methylene_chloride" class="mw-redirect" title="Methylene chloride">methylene chloride</a> to give Schwartz's reagent <sup id="cite_ref-buchwald_3-0" class="reference"><a href="#cite_note-buchwald-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>An alternative procedure that generated Schwartz's reagent from dihydride has also been reported.<sup id="cite_ref-wpif2_4-0" class="reference"><a href="#cite_note-wpif2-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Moreover, it's possible to perform an <i>in situ</i> preparation of (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl from zirconocene dichloride by using LiH. This method can also be used to synthesize isotope-labeled molecules, like olefines by employing Li<sup>2</sup>H or Li<sup>3</sup>H as reducing agents.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Schwartz's reagent has a low solubility in common organic solvents.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The trifluoromethanesulfonate (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrH(OTf) is soluble in THF.<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-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Schwartz%27s_reagent&action=edit&section=2" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The complex adopts the usual "clam-shell" structure seen for other Cp<sub>2</sub>MX<sub>n</sub> complexes.<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 dimetallic structure has been confirmed by <a href="/wiki/Microcrystal_electron_diffraction" title="Microcrystal electron diffraction">Microcrystal electron diffraction</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> The results are consistent with <a href="/wiki/Fourier-transform_infrared_spectroscopy" title="Fourier-transform infrared spectroscopy">FT-IR spectroscopy</a>, which established that the hydrides are bridging. <a href="/wiki/Solid-state_nuclear_magnetic_resonance" title="Solid-state nuclear magnetic resonance">Solid state NMR</a> spectroscopy also indicates a dimeric structure. The X-ray crystallographic structure for the methyl compound (C<sub>5</sub>H<sub>5</sub>)<sub>4</sub>Zr<sub>2</sub>H<sub>2</sub>(CH<sub>3</sub>)<sub>2</sub> compound is analogous.<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> <div class="mw-heading mw-heading2"><h2 id="Uses_in_organic_synthesis">Uses in organic synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Schwartz%27s_reagent&action=edit&section=3" title="Edit section: Uses in organic synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Schwartz's reagent reduces <a href="/wiki/Amide" title="Amide">amides</a> to <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a>.<sup id="cite_ref-leig_11-0" class="reference"><a href="#cite_note-leig-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Vinylation of <a href="/wiki/Ketone" title="Ketone">ketones</a> in high yields is a possible use of Schwartz's reagent.<sup id="cite_ref-li_12-0" class="reference"><a href="#cite_note-li-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Schwartz's reagent has been used in the synthesis of some <a href="/wiki/Macrolide_antibiotics" class="mw-redirect" title="Macrolide antibiotics">macrolide antibiotics</a>,<sup id="cite_ref-duffey_13-0" class="reference"><a href="#cite_note-duffey-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-wu_14-0" class="reference"><a href="#cite_note-wu-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> (−)-motuporin,<sup id="cite_ref-hu_15-0" class="reference"><a href="#cite_note-hu-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> and antitumor agents.<sup id="cite_ref-nic_16-0" class="reference"><a href="#cite_note-nic-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Hydrozirconation">Hydrozirconation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Schwartz%27s_reagent&action=edit&section=4" title="Edit section: Hydrozirconation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b>Hydrozirconation</b> is a form of <a href="/wiki/Hydrometalation" title="Hydrometalation">hydrometalation</a>. Substrates for hydrozirconation are <a href="/wiki/Alkene" title="Alkene">alkenes</a> and <a href="/wiki/Alkyne" title="Alkyne">alkynes</a>. With terminal alkynes the terminal vinyl zirconium product is predominantly formed. Secondary reactions are <a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">nucleophilic additions</a>, <a href="/wiki/Transmetalation" title="Transmetalation">transmetalations</a>,<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> <a href="/wiki/Conjugate_addition" class="mw-redirect" title="Conjugate addition">conjugate additions</a>,<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> <a href="/wiki/Coupling_reaction" title="Coupling reaction">coupling reactions</a>, <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a> and <a href="/wiki/Halogenation" title="Halogenation">halogenation</a>. </p><p><a href="/wiki/Computational_chemistry" title="Computational chemistry">Computational studies</a> indicate that hydrozirconation occurs from the interior portion.<sup id="cite_ref-pank_19-0" class="reference"><a href="#cite_note-pank-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-wang_20-0" class="reference"><a href="#cite_note-wang-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> When treated with one equivalent of Cp<sub>2</sub>ZrClH, <a href="/wiki/Diphenylacetylene" title="Diphenylacetylene">diphenylacetylene</a> gives the corresponding alkenylzirconium as a mixture of <a href="/wiki/Cis_isomer" class="mw-redirect" title="Cis isomer">cis and trans isomers</a>. With two equivalents of hydride, the endproduct was a mixture of <a href="/wiki/Erythro" class="mw-redirect" title="Erythro">erythro</a> and <a href="/wiki/Threo" class="mw-redirect" title="Threo">threo</a> zircono alkanes: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Alkynehydrozirconation1970.svg" class="mw-file-description" title="Alkyne hydrozirconation Weigold 1970"><img alt="Alkyne hydrozirconation Weigold 1970" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Alkynehydrozirconation1970.svg/600px-Alkynehydrozirconation1970.svg.png" decoding="async" width="600" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Alkynehydrozirconation1970.svg/900px-Alkynehydrozirconation1970.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/Alkynehydrozirconation1970.svg/1200px-Alkynehydrozirconation1970.svg.png 2x" data-file-width="723" data-file-height="189" /></a></span></dd></dl> <p>In 1974 Hart and Schwartz reported that the organozirconium intermediates react with <a href="/wiki/Electrophile" title="Electrophile">electrophiles</a> such as <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>, <a href="/wiki/Bromine" title="Bromine">bromine</a> and <a href="/wiki/Acid_chloride" class="mw-redirect" title="Acid chloride">acid chlorides</a> to give the corresponding <a href="/wiki/Alkane" title="Alkane">alkane</a>, <a href="/wiki/Bromoalkane" class="mw-redirect" title="Bromoalkane">bromoalkanes</a>, and <a href="/wiki/Ketone" title="Ketone">ketones</a>:<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> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:AlkenehydrozirconationSchwarz1974.svg" class="mw-file-description" title="Alkene hydrozirconation Schwarz 1974"><img alt="Alkene hydrozirconation Schwarz 1974" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/AlkenehydrozirconationSchwarz1974.svg/600px-AlkenehydrozirconationSchwarz1974.svg.png" decoding="async" width="600" height="219" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/AlkenehydrozirconationSchwarz1974.svg/900px-AlkenehydrozirconationSchwarz1974.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/AlkenehydrozirconationSchwarz1974.svg/1200px-AlkenehydrozirconationSchwarz1974.svg.png 2x" data-file-width="738" data-file-height="269" /></a></span></dd></dl> <p>The corresponding <a href="/wiki/Organoboron" class="mw-redirect" title="Organoboron">organoboron</a> and <a href="/wiki/Organoaluminum" class="mw-redirect" title="Organoaluminum">organoaluminum</a> compounds were already known, but these are air-sensitive and/or <a href="/wiki/Pyrophoric" class="mw-redirect" title="Pyrophoric">pyrophoric</a> whereas organozirconium compounds are not. </p> <div class="mw-heading mw-heading3"><h3 id="Scope">Scope</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Schwartz%27s_reagent&action=edit&section=5" title="Edit section: Scope"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In one study the usual <a href="/wiki/Regioselectivity" title="Regioselectivity">regioselectivity</a> of an alkyne hydrozirconation is reversed with the addition of <a href="/wiki/Zinc_chloride" title="Zinc chloride">zinc chloride</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><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:HydrozirconationReversedregioselectivity.svg" class="mw-file-description" title="Hydrozirconation with reversed regioselectivity Zhang 2007"><img alt="Hydrozirconation with reversed regioselectivity Zhang 2007" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/HydrozirconationReversedregioselectivity.svg/650px-HydrozirconationReversedregioselectivity.svg.png" decoding="async" width="650" height="256" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/HydrozirconationReversedregioselectivity.svg/975px-HydrozirconationReversedregioselectivity.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/HydrozirconationReversedregioselectivity.svg/1300px-HydrozirconationReversedregioselectivity.svg.png 2x" data-file-width="722" data-file-height="284" /></a></span></dd></dl> <p>One example of a <a href="/wiki/One-pot_synthesis" title="One-pot synthesis">one-pot</a> hydrozirconation - carbonylation - coupling is depicted below:<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Hydrozirconationcarbonylationcoupling.svg" class="mw-file-description" title="Hydrozirconation carbonylation coupling Kang 2002"><img alt="Hydrozirconation carbonylation coupling Kang 2002" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Hydrozirconationcarbonylationcoupling.svg/600px-Hydrozirconationcarbonylationcoupling.svg.png" decoding="async" width="600" height="365" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Hydrozirconationcarbonylationcoupling.svg/900px-Hydrozirconationcarbonylationcoupling.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Hydrozirconationcarbonylationcoupling.svg/1200px-Hydrozirconationcarbonylationcoupling.svg.png 2x" data-file-width="722" data-file-height="439" /></a></span></dd></dl> <p>With certain <a href="/wiki/Allyl_alcohol" title="Allyl alcohol">allyl alcohols</a>, the <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> group is replaced by nucleophilic carbon forming a <a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a> ring:<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The selectivity of the hydrozirconation of alkynes has been studied in detail.<sup id="cite_ref-sun_27-0" class="reference"><a href="#cite_note-sun-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-panek_28-0" class="reference"><a href="#cite_note-panek-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Generally, the addition of the Zr–H proceeds via the <i>syn</i>-addition. The rate of addition to unsaturated carbon-carbon bonds is terminal alkyne > <a href="/wiki/Terminal_alkene" title="Terminal alkene">terminal alkene</a> ≈ internal alkyne > disubstituted alkene <sup id="cite_ref-wpif_29-0" class="reference"><a href="#cite_note-wpif-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">Acyl</a> complexes can be generated by insertion of <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">CO</a> into the C–Zr bond resulting from hydrozirconation.<sup id="cite_ref-bertelo_30-0" class="reference"><a href="#cite_note-bertelo-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Upon alkene insertion into the zirconium hydride bond, the resulting zirconium alkyl undergoes facile rearrangement to the terminal alkyl and therefore only terminal acyl compounds can be synthesized in this way. The rearrangement most likely proceeds via β-hydride elimination followed by reinsertion. </p> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Schwartz%27s_reagent&action=edit&section=6" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><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="CITEREFHartSchwartz1974" class="citation journal cs1">Hart, D. W.; Schwartz, J. (1974). "Hydrozirconation. Organic Synthesis via Organozirconium Intermediates. Synthesis and Rearrangement of Alkylzirconium(IV) Complexes and Their Reaction with Electrophiles". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> <b>96</b> (26): 8115–8116. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00833a048">10.1021/ja00833a048</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Hydrozirconation.+Organic+Synthesis+via+Organozirconium+Intermediates.+Synthesis+and+Rearrangement+of+Alkylzirconium%28IV%29+Complexes+and+Their+Reaction+with+Electrophiles&rft.volume=96&rft.issue=26&rft.pages=8115-8116&rft.date=1974&rft_id=info%3Adoi%2F10.1021%2Fja00833a048&rft.aulast=Hart&rft.aufirst=D.+W.&rft.au=Schwartz%2C+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchwartzLabinger2003" class="citation journal cs1">Schwartz, J.; Labinger, J. A. (2003). "Hydrozirconation: A New Transition Metal Reagent for Organic Synthesis". <i><a href="/wiki/Angew._Chem._Int._Ed." class="mw-redirect" title="Angew. Chem. Int. Ed.">Angew. Chem. Int. Ed.</a></i> <b>15</b> (6): 330–340. <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.197603331">10.1002/anie.197603331</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.&rft.atitle=Hydrozirconation%3A+A+New+Transition+Metal+Reagent+for+Organic+Synthesis&rft.volume=15&rft.issue=6&rft.pages=330-340&rft.date=2003&rft_id=info%3Adoi%2F10.1002%2Fanie.197603331&rft.aulast=Schwartz&rft.aufirst=J.&rft.au=Labinger%2C+J.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHartBlackburnSchwartz1975" class="citation journal cs1">Hart, Donald W.; Blackburn, Thomas F.; Schwartz, Jeffrey (1975). "Hydrozirconation. III. Stereospecific and regioselective functionalization of alkylacetylenes via vinylzirconium(IV) intermediates". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. 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Synthesis and Rearrangement of Alkylzirconium(1V) Complexes and Their Reaction with Electrophiles". <i>Journal of the American Chemical Society</i>. <b>96</b> (26): 8115–8116. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00833a048">10.1021/ja00833a048</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+the+American+Chemical+Society&rft.atitle=Hydrozirconation.+Organic+Synthesis+via+Organozirconium+Intermediates.+Synthesis+and+Rearrangement+of+Alkylzirconium%281V%29+Complexes+and+Their+Reaction+with+Electrophiles&rft.volume=96&rft.issue=26&rft.pages=8115-8116&rft.date=1974&rft_id=info%3Adoi%2F10.1021%2Fja00833a048&rft.aulast=Hart&rft.aufirst=D.+W.&rft.au=Schwartz%2C+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" 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="CITEREFZhang2007" class="citation journal cs1">Zhang, Donghui (2007). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2669288">"Directed Hydrozirconation of Propargylic Alcohols"</a>. <i>Journal of the American Chemical Society</i>. <b>129</b> (40): 12088–12089. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja075215o">10.1021/ja075215o</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2669288">2669288</a></span>. <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/17850152">17850152</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+the+American+Chemical+Society&rft.atitle=Directed+Hydrozirconation+of+Propargylic+Alcohols&rft.volume=129&rft.issue=40&rft.pages=12088-12089&rft.date=2007&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2669288%23id-name%3DPMC&rft_id=info%3Apmid%2F17850152&rft_id=info%3Adoi%2F10.1021%2Fja075215o&rft.aulast=Zhang&rft.aufirst=Donghui&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2669288&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" 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">The electrophile in this reaction is <a href="/wiki/Iodine" title="Iodine">iodine</a>. The additive is believed to promote <a href="/wiki/Kinetic_reaction_control" class="mw-redirect" title="Kinetic reaction control">kinetic reaction control</a>.</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="CITEREFKang2002" class="citation journal cs1">Kang, Suk-Ku (2002). "Palladium-catalyzed coupling reaction of acylzirconocene chlorides with hypervalent iodonium salts: synthesis of aryl-substituted ketones". <i>Journal of the Chemical Society, Perkin Transactions 1</i> (4): 459–461. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fb110983a">10.1039/b110983a</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+the+Chemical+Society%2C+Perkin+Transactions+1&rft.atitle=Palladium-catalyzed+coupling+reaction+of+acylzirconocene+chlorides+with+hypervalent+iodonium+salts%3A+synthesis+of+aryl-substituted+ketones&rft.issue=4&rft.pages=459-461&rft.date=2002&rft_id=info%3Adoi%2F10.1039%2Fb110983a&rft.aulast=Kang&rft.aufirst=Suk-Ku&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text">Reagents: <a href="/wiki/Phenylacetylene" title="Phenylacetylene">phenylacetylene</a>, Schwartz's reagent, <a href="/w/index.php?title=Tetraphenylpalladium&action=edit&redlink=1" class="new" title="Tetraphenylpalladium (page does not exist)">tetraphenylpalladium</a> and the <a href="/wiki/Iodane" class="mw-redirect" title="Iodane">iodane</a> <a href="/w/index.php?title=Diphenyliodonium&action=edit&redlink=1" class="new" title="Diphenyliodonium (page does not exist)">diphenyliodonium</a><a href="/wiki/Tetrafluoroborate" title="Tetrafluoroborate">tetrafluoroborate</a> (<a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> group donor)</span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGandon2002" class="citation journal cs1">Gandon, Vincent (2002). "A one-pot access to cyclopropanes from allylic ethers via hydrozirconation–deoxygenative ring formation". <i>Chemical Communications</i> (12): 1308–1309. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fb203762a">10.1039/b203762a</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/12109129">12109129</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Communications&rft.atitle=A+one-pot+access+to+cyclopropanes+from+allylic+ethers+via+hydrozirconation%E2%80%93deoxygenative+ring+formation&rft.issue=12&rft.pages=1308-1309&rft.date=2002&rft_id=info%3Adoi%2F10.1039%2Fb203762a&rft_id=info%3Apmid%2F12109129&rft.aulast=Gandon&rft.aufirst=Vincent&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" class="Z3988"></span></span> </li> <li id="cite_note-sun-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-sun_27-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSunOkabeCoffenSchwartz1998" class="citation journal cs1">Sun, R. C.; Okabe, M.; Coffen, D. L.; Schwartz, J. (1998). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv9p0640">"Conjugate Addition of a Vinylzirconium Reagent: 3-(1-Octene-1-yl)cyclopentanone"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Conjugate+Addition+of+a+Vinylzirconium+Reagent%3A+3-%281-Octene-1-yl%29cyclopentanone&rft.date=1998&rft.aulast=Sun&rft.aufirst=R.+C.&rft.au=Okabe%2C+M.&rft.au=Coffen%2C+D.+L.&rft.au=Schwartz%2C+J.&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dcv9p0640&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol. 9, p. 640</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=640&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" class="Z3988"></span>.</span> </li> <li id="cite_note-panek-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-panek_28-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPanekHu1997" class="citation journal cs1">Panek, J. S.; Hu, T. (1997). "Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction". <i><a href="/wiki/J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a></i> <b>62</b> (15): 4912–4913. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo970647a">10.1021/jo970647a</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=Stereo-+and+Regiocontrolled+Synthesis+of+Branched+Trisubstituted+Conjugated+Dienes+by+Palladium%280%29-Catalyzed+Cross-Coupling+Reaction&rft.volume=62&rft.issue=15&rft.pages=4912-4913&rft.date=1997&rft_id=info%3Adoi%2F10.1021%2Fjo970647a&rft.aulast=Panek&rft.aufirst=J.+S.&rft.au=Hu%2C+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" class="Z3988"></span></span> </li> <li id="cite_note-wpif-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-wpif_29-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWipfJahn1996" class="citation journal cs1">Wipf, Peter; Jahn, Heike (1996). "Synthetic applications of organochlorozirconocene complexes". <i><a href="/wiki/Tetrahedron_(journal)" title="Tetrahedron (journal)">Tetrahedron</a></i>. <b>52</b> (40): 12853–12910. <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%2F0040-4020%2896%2900754-5">10.1016/0040-4020(96)00754-5</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Synthetic+applications+of+organochlorozirconocene+complexes&rft.volume=52&rft.issue=40&rft.pages=12853-12910&rft.date=1996&rft_id=info%3Adoi%2F10.1016%2F0040-4020%2896%2900754-5&rft.aulast=Wipf&rft.aufirst=Peter&rft.au=Jahn%2C+Heike&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" class="Z3988"></span></span> </li> <li id="cite_note-bertelo-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-bertelo_30-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBerteloSchwartz1975" class="citation journal cs1">Bertelo, Christopher A.; Schwartz, Jeffrey (1975). "Hydrozirconation. II. Oxidative homologation of olefins via carbon monoxide insertion into the carbon-zirconium bond". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> <b>97</b> (1): 228–230. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00834a061">10.1021/ja00834a061</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Hydrozirconation.+II.+Oxidative+homologation+of+olefins+via+carbon+monoxide+insertion+into+the+carbon-zirconium+bond&rft.volume=97&rft.issue=1&rft.pages=228-230&rft.date=1975&rft_id=info%3Adoi%2F10.1021%2Fja00834a061&rft.aulast=Bertelo&rft.aufirst=Christopher+A.&rft.au=Schwartz%2C+Jeffrey&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchwartz%27s+reagent" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Schwartz%27s_reagent&action=edit&section=8" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cyclopentadienide_complexes" title="Template:Cyclopentadienide complexes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cyclopentadienide_complexes" title="Template talk:Cyclopentadienide complexes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cyclopentadienide_complexes" title="Special:EditPage/Template:Cyclopentadienide complexes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Salts_and_covalent_derivatives_of_the_cyclopentadienide_ion" style="font-size:114%;margin:0 4em">Salts and covalent derivatives of the <a href="/wiki/Cyclopentadienide" class="mw-redirect" title="Cyclopentadienide">cyclopentadienide</a> ion</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto"> <table class="center"> <tbody><tr style="background-color:mistyrose"> <td><a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">CpH</a> </td> <td style="background-color:white;border:none"> </td> <td style="background-color:white;border:none" colspan="11" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="5"> </td> <td>He </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Lithium_cyclopentadienide" title="Lithium cyclopentadienide">LiCp</a> </td> <td>Be </td> <td>B </td> <td><a href="/wiki/Methylcyclopentadiene" title="Methylcyclopentadiene">CpMe</a> </td> <td>N </td> <td><a href="/wiki/Cyclopentadienone" title="Cyclopentadienone">C<sub>5</sub>H<sub>4</sub>O</a> </td> <td>F </td> <td>Ne </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Sodium_cyclopentadienide" title="Sodium cyclopentadienide">NaCp</a> </td> <td><a href="/wiki/Magnesocene" title="Magnesocene">MgCp<sub>2</sub></a><br /> <p><a href="/wiki/Cyclopentadienyl_magnesium_bromide" title="Cyclopentadienyl magnesium bromide">MgCpBr</a> </p> </td> <td>Al </td> <td>Si </td> <td>P </td> <td>S </td> <td>Cl </td> <td>Ar </td></tr> <tr style="background-color:mistyrose"> <td>K </td> <td><a href="/wiki/Calcium_cyclopentadienylide" class="mw-redirect" title="Calcium cyclopentadienylide">CaCp<sub>2</sub></a> </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Scandocene" title="Scandocene">ScCp<sub>3</sub></a> </td> <td><a href="/wiki/Titanocene_dichloride" title="Titanocene dichloride">TiCp<sub>2</sub>Cl<sub>2</sub></a><br /> <p><a href="/wiki/Nugent-RajanBabu_reagent" class="mw-redirect" title="Nugent-RajanBabu reagent">(TiCp<sub>2</sub>Cl)<sub>2</sub></a><br /> <a href="/wiki/(Cyclopentadienyl)titanium_trichloride" title="(Cyclopentadienyl)titanium trichloride">TiCpCl<sub>3</sub></a><br /> <a href="/wiki/Titanocene_pentasulfide" title="Titanocene pentasulfide">TiCp<sub>2</sub>S<sub>5</sub></a><br /> <a href="/wiki/Titanocene_dicarbonyl" title="Titanocene dicarbonyl">TiCp<sub>2</sub>(CO)<sub>2</sub></a><br /> <a href="/wiki/Petasis_reagent" title="Petasis reagent">TiCp<sub>2</sub>Me<sub>2</sub></a> </p> </td> <td><a href="/wiki/Vanadocene" title="Vanadocene">VCp<sub>2</sub></a><br /> <p><a href="/wiki/(Cycloheptatrienyl)(cyclopentadienyl)vanadium" title="(Cycloheptatrienyl)(cyclopentadienyl)vanadium">VCpCh</a><br /> <a href="/wiki/Vanadocene_dichloride" title="Vanadocene dichloride">VCp<sub>2</sub>Cl<sub>2</sub></a><br /> <a href="/wiki/Cyclopentadienylvanadium_tetracarbonyl" title="Cyclopentadienylvanadium tetracarbonyl">VCp(CO)<sub>4</sub></a> </p> </td> <td><a href="/wiki/Chromocene" title="Chromocene">CrCp<sub>2</sub></a><br /> <p><a href="/wiki/Cyclopentadienylchromium_tricarbonyl_dimer" title="Cyclopentadienylchromium tricarbonyl dimer">(CrCp(CO)<sub>3</sub>)<sub>2</sub></a> </p> </td> <td><a href="/wiki/Manganocene" title="Manganocene">MnCp<sub>2</sub></a> </td> <td><a href="/wiki/Ferrocene" title="Ferrocene">FeCp<sub>2</sub></a><br /> <p><a href="/wiki/1,1%27-Dilithioferrocene" title="1,1'-Dilithioferrocene">Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>4</sub>Li)<sub>2</sub></a><br /> <a href="/wiki/Biferrocene" title="Biferrocene">((C<sub>5</sub>H<sub>5</sub>)Fe(C<sub>5</sub>H<sub>4</sub>))<sub>2</sub></a><br /> <a href="/wiki/Bis(fulvalene)diiron" title="Bis(fulvalene)diiron">(C<sub>5</sub>H<sub>4</sub>-C<sub>5</sub>H<sub>4</sub>)<sub>2</sub>Fe<sub>2</sub></a><br /> <a href="/wiki/Ferrocenium_hexafluorophosphate" title="Ferrocenium hexafluorophosphate">FeCp<sub>2</sub>PF<sub>6</sub></a><br /> <a href="/wiki/Cyclopentadienyliron_dicarbonyl_iodide" title="Cyclopentadienyliron dicarbonyl iodide">FeCp(CO)<sub>2</sub>I</a> </p> </td> <td><a href="/wiki/Cobaltocene" title="Cobaltocene">CoCp<sub>2</sub></a><br /> <p><a href="/wiki/Cyclopentadienylcobalt_dicarbonyl" title="Cyclopentadienylcobalt dicarbonyl">CoCp(CO)<sub>2</sub></a> </p> </td> <td><a href="/wiki/Nickelocene" title="Nickelocene">NiCp<sub>2</sub></a><br /> <p><a href="/wiki/Cyclopentadienyl_nickel_nitrosyl" title="Cyclopentadienyl nickel nitrosyl">NiCpNO</a> </p> </td> <td>Cu </td> <td>Zn </td> <td>Ga </td> <td>Ge </td> <td>As </td> <td>Se </td> <td>Br </td> <td>Kr </td></tr> <tr style="background-color:mistyrose"> <td>Rb </td> <td>Sr </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Yttrocene" title="Yttrocene">Y(C<sub>5</sub>H<sub>5</sub>)<sub>3</sub></a> </td> <td><a href="/wiki/Zirconocene_dichloride" title="Zirconocene dichloride">ZrCp<sub>2</sub>Cl<sub>2</sub></a><br /> <p><a class="mw-selflink selflink">ZrCp<sub>2</sub>ClH</a> </p> </td> <td><a href="/wiki/Niobocene_dichloride" title="Niobocene dichloride">NbCp<sub>2</sub>Cl<sub>2</sub></a> </td> <td><a href="/wiki/Molybdocene_dihydride" title="Molybdocene dihydride">MoCp<sub>2</sub>H<sub>2</sub></a><br /> <p><a href="/wiki/Molybdocene_dichloride" title="Molybdocene dichloride">MoCp<sub>2</sub>Cl<sub>2</sub></a><br /> <a href="/wiki/Cyclopentadienylmolybdenum_tricarbonyl_dimer" title="Cyclopentadienylmolybdenum tricarbonyl dimer">(MoCp(CO)<sub>3</sub>)<sub>2</sub></a> </p> </td> <td>Tc </td> <td><a href="/wiki/Ruthenocene" title="Ruthenocene">RuCp<sub>2</sub></a><br /> <p><a href="/wiki/Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium" title="Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium">RuCp(PPh<sub>3</sub>)<sub>2</sub>Cl</a><br /> <a href="/wiki/Tris(acetonitrile)cyclopentadienylruthenium_hexafluorophosphate" title="Tris(acetonitrile)cyclopentadienylruthenium hexafluorophosphate">RuCp(MeCN)<sub>3</sub>PF<sub>6</sub></a> </p> </td> <td><a href="/wiki/Rhodocene" title="Rhodocene">RhCp<sub>2</sub></a> </td> <td><a href="/wiki/Cyclopentadienyl_allyl_palladium" title="Cyclopentadienyl allyl palladium">PdCp(C<sub>3</sub>H<sub>5</sub>)</a> </td> <td>Ag </td> <td>Cd </td> <td><a href="/wiki/Cyclopentadienylindium(I)" title="Cyclopentadienylindium(I)">InCp</a> </td> <td><a href="/wiki/Stannocene" title="Stannocene">SnCp<sub>2</sub></a> </td> <td>Sb </td> <td>Te </td> <td>I </td> <td>Xe </td></tr> <tr style="background-color:mistyrose"> <td>Cs </td> <td>Ba </td> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">LuCp<sub>3</sub></a> </td> <td><a href="/wiki/Hafnocene_dichloride" title="Hafnocene dichloride">HfCp<sub>2</sub>Cl<sub>2</sub></a> </td> <td>Ta </td> <td><a href="/wiki/Cyclopentadienyltungsten_tricarbonyl_dimer" title="Cyclopentadienyltungsten tricarbonyl dimer">(WCp(CO)<sub>3</sub>)<sub>2</sub></a> </td> <td><a href="/wiki/Rhenocene" class="mw-redirect" title="Rhenocene">ReCp<sub>2</sub>H</a> </td> <td><a href="/wiki/Osmocene" title="Osmocene">OsCp<sub>2</sub></a> </td> <td><a href="/wiki/Iridocene" class="mw-redirect" title="Iridocene">IrCp<sub>2</sub></a> </td> <td>Pt </td> <td>Au </td> <td>Hg </td> <td><a href="/wiki/Cyclopentadienylthallium" title="Cyclopentadienylthallium">TlCp</a> </td> <td><a href="/wiki/Plumbocene" title="Plumbocene">PbCp<sub>2</sub></a> </td> <td>Bi </td> <td>Po </td> <td>At </td> <td>Rn </td></tr> <tr style="background-color:mistyrose"> <td>Fr </td> <td>Ra </td> <td style="background-color:white;border:none">** </td> <td>Lr </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td><a href="/wiki/Hassocene" class="mw-redirect" title="Hassocene">HsCp<sub>2</sub></a> </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="background-color:white;border:none" colspan="2" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="20">  </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">LaCp<sub>3</sub></a> </td> <td><a href="/wiki/Cerocene" title="Cerocene">CeCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">PrCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">NdCp<sub>3</sub></a> </td> <td><a href="/wiki/Promethocene" title="Promethocene">PmCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">SmCp<sub>3</sub></a> </td> <td>Eu </td> <td>Gd </td> <td>Tb </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">DyCp<sub>3</sub></a> </td> <td>Ho </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">ErCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">TmCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">YbCp<sub>3</sub></a> </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">** </td> <td>Ac </td> <td><a 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