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Transition metal formyl complex
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<h2 id="structure-and-bonding">Structure and bonding</h2> <p>The MCHO group is planar. A C=O <a href="/facts/Double_bond/qDemMn0c">double bond</a> is indicated by <a href="/facts/X-ray_crystallography/WtI0F5DN">X-ray crystallography</a>. A second resonance structure has a M=C double bond, with negative charge on oxygen. </p> <h2 id="synthesis-and-reactions">Synthesis and reactions</h2> <p>Metal formyl complexes are often prepared by the reaction of metal carbonyls with hydride reagents:<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> </p> [Re(CO)6]+ + H− → (CO)5ReCHO <p>The CO ligand is the electrophile and the hydride (provided typically from a <a href="/facts/Borohydride/5zFNIPw7">borohydride</a>) is the nucleophile. </p><p>Some metal formyls are produced by reaction of metal carbonyl anions with reagents that donate the equivalent of a formyl cation, such a mixed formate anhydrides.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> </p><p>Metal formyls participate in many reactions, many of which are motivated by interest in Fischer-Tropsch chemistry. O-alkylation gives carbenoid complexes. The formyl ligand also functions as a base, allowing the formation of M-CH=O-M' linkages.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> Decarbonylation leads to de-insertion of the carbonyl, yielding hydride complexes.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Gladysz, J.A. (1982). Transition Metal Formyl Complexes. Advances in Organometallic Chemistry. Vol. 20. pp. 1–38. doi:10.1016/S0065-3055(08)60519-5. ISBN 9780120311200. <a href="9780120311200" target="_blank">9780120311200</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Maity, Ayan; Teets, Thomas S. (2016). "Main Group Lewis Acid-Mediated Transformations of Transition-Metal Hydride Complexes". Chemical Reviews. 116 (15): 8873–8911. doi:10.1021/acs.chemrev.6b00034. PMID 27164024. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Collman, J. P.; Winter, S. R. (1973). "Isolation and Characterization of a Kinetically Stable transition Metal Formyl complex". Journal of the American Chemical Society. 95 (12): 4089–4090. doi:10.1021/ja00793a066. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Chen, Zilu; Schmalle, Helmut W.; Fox, Thomas; Berke, Heinz (2005). "Insertion Reactions of Hydridonitrosyltetrakis(trimethylphosphine) Tungsten(0)". Dalton Transactions (3): 580–587. doi:10.1039/b414943b. PMID 15672204. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Gladysz, J.A. (1982). Transition Metal Formyl Complexes. Advances in Organometallic Chemistry. Vol. 20. pp. 1–38. doi:10.1016/S0065-3055(08)60519-5. ISBN 9780120311200. <a href="9780120311200" target="_blank">9780120311200</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> </ol>