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Electrophilic Substitution Reactions of Metallabenzynes

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Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong
Cite this: J. Am. Chem. Soc. 2011, 133, 45, 18350–18360
Publication Date (Web):October 13, 2011
https://doi.org/10.1021/ja207315h
Copyright © 2011 American Chemical Society

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    The electrophilic substitution reactions of metallabenzynes Os(≡CC(R)═C(CH3)C(R)═CH)Cl2(PPh3)2 (R = SiMe3, H) were studied. These metallabenzynes react with electrophilic reagents, including Br2, NO2BF4, NOBF4, HCl/H2O2, and AlCl3/H2O2 to afford the corresponding bromination, nitration, nitrosation, and chlorination products. The reactions usually occur at the C2 and C4 positions of the metallacycle. These observations support the notion that metallabenzynes exhibit aromatic properties.

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    Text giving the complete ref 38, tables giving Cartesian coordinates and electronic energies for all the calculated structures, and CIF files giving X-ray crystallographic data for 37 and 9. This material is available free of charge via the Internet at http://pubs.acs.org.

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