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<div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Ferrocenecarboxaldehyde </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:FcCHO.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/FcCHO.svg/120px-FcCHO.svg.png" decoding="async" width="120" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/FcCHO.svg/180px-FcCHO.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/52/FcCHO.svg/240px-FcCHO.svg.png 2x" data-file-width="126" data-file-height="77" /></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;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">FcCHO, Formylferrocene</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=12093-10-6">12093-10-6</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-%5D1C%3DCC%3DC1.C1%3DC%5BC-%5D%28C%3DC1%29C%3DO.%5BFe%2B2%5D">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28%3DO%29%5BC-%5D12%5BFe%2B2%5D3456789%28%5BCH%5D1%3D%5BCH%5D3%5BCH%5D4%3D%5BCH%5D52%29%5BCH-%5D%2510%5BCH%5D6%3D%5BCH%5D7%5BCH%5D8%3D%5BCH%5D9%2510">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.26585886.html">26585886</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/100.031.950">100.031.950</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q30943857#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><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/15184314">15184314</a></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/C6H5O.C5H5.Fe/c7-5-6-3-1-2-4-6;1-2-4-5-3-1;/h1-5H;1-5H;/q2*-1;+2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MQHZGUNMWQBVDK-UHFFFAOYSA-N</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=1S/C6H5O.C5H5.Fe/c7-5-6-3-1-2-4-6;1-2-4-5-3-1;/h1-5H;1-5H;/q2*-1;+2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MQHZGUNMWQBVDK-UHFFFAOYSA-N</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-]1C=CC=C1.C1=C[C-](C=C1)C=O.[Fe+2]</div></li><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%;">C(=O)[C-]12[Fe+2]3456789([CH]1=[CH]3[CH]4=[CH]52)[CH-]%10[CH]6=[CH]7[CH]8=[CH]9%10</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><span title="Carbon">C</span><sub>11</sub><span title="Hydrogen">H</span><sub>10</sub><span title="Iron">Fe</span><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002214045000000000♠"></span>214.045</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>orange solid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.566 g/cm<sup>3</sup><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> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>118–120 °C (244–248 °F; 391–393 K) </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> <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>Ferrocenecarboxaldehyde</b> is the <a href="/wiki/Organoiron_compound" class="mw-redirect" title="Organoiron compound">organoiron compound</a> with 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">5</sub>H<sub class="template-chem2-sub">5</sub>)Fe(C<sub class="template-chem2-sub">5</sub>HCHO)</span>. The molecule consists of <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a> substituted by an <a href="/wiki/Formyl_group" class="mw-redirect" title="Formyl group">formyl group</a> on one of the <a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a> rings. It is an orange, air-stable solid that is soluble in organic solvents. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferrocenecarboxaldehyde&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ferrocenecarboxaldehyde is prepared by <a href="/wiki/Vilsmeier-Haack_reaction" class="mw-redirect" title="Vilsmeier-Haack reaction">Vilsmeier-Haack reaction</a> (formylation) using <a href="/wiki/Dimethylformamide" title="Dimethylformamide">dimethylformamide</a> and <a href="/wiki/Phosphorus_oxychloride" class="mw-redirect" title="Phosphorus oxychloride">phosphorus oxychloride</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> Diformylation does not occur readily.<sup id="cite_ref-Rausch_3-0" class="reference"><a href="#cite_note-Rausch-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>According to <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> ferrocenecarboxaldehyde adopts the expected sandwich structure exhibited by other ferrocenes. The formyl group is coplanar with its attached ring.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>In its IR spectrum, ferrocenecarboxaldehyde is characterized by a low frequency ν<sub>CO</sub> band at 1670 cm<sup>-1</sup> vs 1704 cm<sup>-1</sup> for <a href="/wiki/Benzaldehyde" title="Benzaldehyde">benzaldehyde</a>.<sup id="cite_ref-Rausch_3-1" class="reference"><a href="#cite_note-Rausch-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferrocenecarboxaldehyde&action=edit&section=2" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ferrocenecarboxaldehyde behaves like other aldehydes in terms of its reactivity, the main difference is that it is electroactive. Its basicity is indicated by the solubility of the compound in hydrochloric acid.<sup id="cite_ref-Rausch_3-2" class="reference"><a href="#cite_note-Rausch-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Ferrocenecarboxaldehyde, owing to the versatility of the formyl group, is a precursor to many ferrocene-modified compounds. With a <a href="/wiki/Wittig_reagent" class="mw-redirect" title="Wittig reagent">Wittig reagent</a>, it converts to <a href="/wiki/Vinylferrocene" title="Vinylferrocene">vinylferrocene</a> and related derivatives.<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> With <a href="/wiki/Primary_amine" class="mw-redirect" title="Primary amine">primary amines</a>, ferrocenecarboxaldehyde condenses to give <a href="/wiki/Imine" title="Imine">imines</a>. The <a href="/wiki/Azomethine" class="mw-redirect" title="Azomethine">azomethine</a> derivative undergoes 1,3-cycloaddition to C<sub>60</sub>.<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> </p><p>It can be reduced to the corresponding alcohol with hydride reducing agents.<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> Asymmetric alkylation gives the chiral α-hydroxyethylferrocene.<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> <a href="/wiki/Dioxane" class="mw-redirect" title="Dioxane">Dioxane</a> derivatives, obtainable from 1,3-diols and the aldehyde, sustain <a href="/wiki/Directed_ortho_metalation" title="Directed ortho metalation">ortho lithiation</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> </p> <div class="mw-heading mw-heading2"><h2 id="Related_compounds">Related compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferrocenecarboxaldehyde&action=edit&section=3" title="Edit section: Related compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Ferrocenecarboxylic_acid" title="Ferrocenecarboxylic acid">ferrocenecarboxylic acid</a></li> <li><a href="/w/index.php?title=Ferrocenemethanol&action=edit&redlink=1" class="new" title="Ferrocenemethanol (page does not exist)">ferrocenemethanol</a></li> <li><a href="/wiki/Acetylferrocene" title="Acetylferrocene">acetylferrocene</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferrocenecarboxaldehyde&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><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="CITEREFSatoIwaiSanoKonno1984" class="citation journal cs1">Sato, Kumiko; Iwai, Makoto; Sano, Hirotoshi; Konno, Michiko (1984). "Plastic Phase of Formylferrocene Studied by X-Ray Diffraction and Mössbauer Spectroscopy". <i>Bulletin of the Chemical Society of Japan</i>. <b>57</b> (3): 634–638. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.57.634">10.1246/bcsj.57.634</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+of+the+Chemical+Society+of+Japan&rft.atitle=Plastic+Phase+of+Formylferrocene+Studied+by+X-Ray+Diffraction+and+M%C3%B6ssbauer+Spectroscopy&rft.volume=57&rft.issue=3&rft.pages=634-638&rft.date=1984&rft_id=info%3Adoi%2F10.1246%2Fbcsj.57.634&rft.aulast=Sato&rft.aufirst=Kumiko&rft.au=Iwai%2C+Makoto&rft.au=Sano%2C+Hirotoshi&rft.au=Konno%2C+Michiko&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocenecarboxaldehyde" 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="CITEREFGrahamLindseyParshallPeterson1957" class="citation journal cs1">Graham, P. J.; Lindsey, R. V.; Parshall, G. W.; Peterson, M. L.; Whitman, G. M. (1957). "Some Acyl Ferrocenes and their Reactions". <i>Journal of the American Chemical Society</i>. <b>79</b> (13): 3416–3420. <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%2Fja01570a027">10.1021/ja01570a027</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=Some+Acyl+Ferrocenes+and+their+Reactions&rft.volume=79&rft.issue=13&rft.pages=3416-3420&rft.date=1957&rft_id=info%3Adoi%2F10.1021%2Fja01570a027&rft.aulast=Graham&rft.aufirst=P.+J.&rft.au=Lindsey%2C+R.+V.&rft.au=Parshall%2C+G.+W.&rft.au=Peterson%2C+M.+L.&rft.au=Whitman%2C+G.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocenecarboxaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-Rausch-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Rausch_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Rausch_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Rausch_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRausch1963" class="citation journal cs1">Rausch, M. D. (1963). "Metallocene Chemistry—A Decade of Progress". <i>Canadian Journal of Chemistry</i>. <b>41</b> (5): 1289–1314. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fv63-182">10.1139/v63-182</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Canadian+Journal+of+Chemistry&rft.atitle=Metallocene+Chemistry%E2%80%94A+Decade+of+Progress&rft.volume=41&rft.issue=5&rft.pages=1289-1314&rft.date=1963&rft_id=info%3Adoi%2F10.1139%2Fv63-182&rft.aulast=Rausch&rft.aufirst=M.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocenecarboxaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLousadaPintoCanongia_LopesMinas_Da_Piedade2008" class="citation journal cs1">Lousada, Cláudio M.; Pinto, Susana S.; Canongia Lopes, José N.; Minas Da Piedade, M. Fátima; Diogo, Hermínio P.; Minas Da Piedade, Manuel E. (2008). "Experimental and Molecular Dynamics Simulation Study of the Sublimation and Vaporization Energetics of Iron Metalocenes. Crystal Structures of Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>4</sub>CH<sub>3</sub>)<sub>2</sub>and Fe[(η<sup>5</sup>-(C<sub>5</sub>H<sub>5</sub>)(η<sup>5</sup>-C<sub>5</sub>H<sub>4</sub>CHO)]". <i>The Journal of Physical Chemistry A</i>. <b>112</b> (13): 2977–2987. <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%2Fjp7107818">10.1021/jp7107818</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/18331009">18331009</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Physical+Chemistry+A&rft.atitle=Experimental+and+Molecular+Dynamics+Simulation+Study+of+the+Sublimation+and+Vaporization+Energetics+of+Iron+Metalocenes.+Crystal+Structures+of+Fe%28%CE%B7%3Csup%3E5%3C%2Fsup%3E-C%3Csub%3E5%3C%2Fsub%3EH%3Csub%3E4%3C%2Fsub%3ECH%3Csub%3E3%3C%2Fsub%3E%29%3Csub%3E2%3C%2Fsub%3Eand+Fe%26%2391%3B%28%CE%B7%3Csup%3E5%3C%2Fsup%3E-%28C%3Csub%3E5%3C%2Fsub%3EH%3Csub%3E5%3C%2Fsub%3E%29%28%CE%B7%3Csup%3E5%3C%2Fsup%3E-C%3Csub%3E5%3C%2Fsub%3EH%3Csub%3E4%3C%2Fsub%3ECHO%29%26%2393%3B&rft.volume=112&rft.issue=13&rft.pages=2977-2987&rft.date=2008&rft_id=info%3Adoi%2F10.1021%2Fjp7107818&rft_id=info%3Apmid%2F18331009&rft.aulast=Lousada&rft.aufirst=Cl%C3%A1udio+M.&rft.au=Pinto%2C+Susana+S.&rft.au=Canongia+Lopes%2C+Jos%C3%A9+N.&rft.au=Minas+Da+Piedade%2C+M.+F%C3%A1tima&rft.au=Diogo%2C+Herm%C3%ADnio+P.&rft.au=Minas+Da+Piedade%2C+Manuel+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocenecarboxaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLiuXuMaLiang2001" class="citation journal cs1">Liu WY, Xu QH, Ma YX, Liang YM, Dong NL, Guan DP (2001). "Solvent-free synthesis of ferrocenylethene derivatives". <i><a href="/wiki/Journal_of_Organometallic_Chemistry" title="Journal of Organometallic Chemistry">J. Organomet. Chem.</a></i> <b>625</b>: 128–132. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0022-328X%2800%2900927-X">10.1016/S0022-328X(00)00927-X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Organomet.+Chem.&rft.atitle=Solvent-free+synthesis+of+ferrocenylethene+derivatives&rft.volume=625&rft.pages=128-132&rft.date=2001&rft_id=info%3Adoi%2F10.1016%2FS0022-328X%2800%2900927-X&rft.aulast=Liu&rft.aufirst=WY&rft.au=Xu%2C+QH&rft.au=Ma%2C+YX&rft.au=Liang%2C+YM&rft.au=Dong%2C+NL&rft.au=Guan%2C+DP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocenecarboxaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMagginiScorranoPrato1993" class="citation journal cs1">Maggini, Michele; Scorrano, Gianfranco; Prato, Maurizio (1993). "Addition of Azomethine Ylides to C<sub>60</sub>: Synthesis, Characterization, and Functionalization of Fullerene Pyrrolidines". <i>Journal of the American Chemical Society</i>. <b>115</b> (21): 9798–9799. <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%2Fja00074a056">10.1021/ja00074a056</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=Addition+of+Azomethine+Ylides+to+C%3Csub%3E60%3C%2Fsub%3E%3A+Synthesis%2C+Characterization%2C+and+Functionalization+of+Fullerene+Pyrrolidines&rft.volume=115&rft.issue=21&rft.pages=9798-9799&rft.date=1993&rft_id=info%3Adoi%2F10.1021%2Fja00074a056&rft.aulast=Maggini&rft.aufirst=Michele&rft.au=Scorrano%2C+Gianfranco&rft.au=Prato%2C+Maurizio&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocenecarboxaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLednicerMashburn,_Jr.Hauser1960" class="citation journal cs1">Lednicer, Daniel; Mashburn, Jr., T. Arthur; Hauser, Charles R. (1960). "Hydroxymethylferrocene". <i>Organic Syntheses</i>. <b>40</b>: 52. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.040.0052">10.15227/orgsyn.040.0052</a>.</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=Hydroxymethylferrocene&rft.volume=40&rft.pages=52&rft.date=1960&rft_id=info%3Adoi%2F10.15227%2Forgsyn.040.0052&rft.aulast=Lednicer&rft.aufirst=Daniel&rft.au=Mashburn%2C+Jr.%2C+T.+Arthur&rft.au=Hauser%2C+Charles+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocenecarboxaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKitamuraOkaSugaNoyori2002" class="citation journal cs1">Kitamura, Masato; Oka, Hiromasa; Suga, Seiji; Noyori, Ryoji (2002). "Catalytic Enantioselective Addition of Dialkylzincs To Aldehydes Using (2S)-(−)-3-exo-(Dimethylamino)isoborneol: (S)-1-Phenyl-1-propanol". <i>Organic Syntheses</i>. <b>79</b>: 139. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.079.0139">10.15227/orgsyn.079.0139</a>.</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=Catalytic+Enantioselective+Addition+of+Dialkylzincs+To+Aldehydes+Using+%282S%29-%28%E2%88%92%29-3-exo-%28Dimethylamino%29isoborneol%3A+%28S%29-1-Phenyl-1-propanol&rft.volume=79&rft.pages=139&rft.date=2002&rft_id=info%3Adoi%2F10.15227%2Forgsyn.079.0139&rft.aulast=Kitamura&rft.aufirst=Masato&rft.au=Oka%2C+Hiromasa&rft.au=Suga%2C+Seiji&rft.au=Noyori%2C+Ryoji&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocenecarboxaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRiantSamuelFlessnerTaudien1997" class="citation journal cs1">Riant, Olivier; Samuel, Odile; Flessner, Timo; Taudien, Stephan; Kagan, Henri B. (1997). "An Efficient Asymmetric Synthesis of 2-Substituted Ferrocenecarboxaldehydes". <i>The Journal of Organic Chemistry</i>. <b>62</b> (20): 6733–6745. <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%2Fjo970075u">10.1021/jo970075u</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=An+Efficient+Asymmetric+Synthesis+of+2-Substituted+Ferrocenecarboxaldehydes&rft.volume=62&rft.issue=20&rft.pages=6733-6745&rft.date=1997&rft_id=info%3Adoi%2F10.1021%2Fjo970075u&rft.aulast=Riant&rft.aufirst=Olivier&rft.au=Samuel%2C+Odile&rft.au=Flessner%2C+Timo&rft.au=Taudien%2C+Stephan&rft.au=Kagan%2C+Henri+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFerrocenecarboxaldehyde" class="Z3988"></span></span> </li> </ol></div></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=Ferrocenecarboxaldehyde&action=edit&section=5" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Ferrocenecarboxaldehyde&oldid=1255105289">https://en.wikipedia.org/w/index.php?title=Ferrocenecarboxaldehyde&oldid=1255105289</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Ferrocenes" title="Category:Ferrocenes">Ferrocenes</a></li><li><a href="/wiki/Category:Cyclopentadienyl_complexes" title="Category:Cyclopentadienyl complexes">Cyclopentadienyl complexes</a></li><li><a href="/wiki/Category:Aldehydes" title="Category:Aldehydes">Aldehydes</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Chemical_articles_with_multiple_compound_IDs" title="Category:Chemical articles with multiple compound IDs">Chemical articles with multiple compound IDs</a></li><li><a href="/wiki/Category:Multiple_chemicals_in_an_infobox_that_need_indexing" title="Category:Multiple chemicals in an infobox that need indexing">Multiple chemicals in an infobox that need indexing</a></li><li><a href="/wiki/Category:Articles_without_EBI_source" title="Category:Articles without EBI source">Articles without EBI source</a></li><li><a href="/wiki/Category:Articles_without_KEGG_source" title="Category:Articles without KEGG source">Articles without KEGG source</a></li><li><a href="/wiki/Category:Articles_without_UNII_source" title="Category:Articles without UNII source">Articles without UNII source</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Chembox_image_size_set" title="Category:Chembox image size set">Chembox image size set</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 3 November 2024, at 04:40<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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