The Journal of Organic Chemistry

Formation and reactivity of. sigma.-radical cation intermediates in the carbon-carbon coupling reaction of phenyldiazomethanes by one-electron oxidation

K Ishiguro, M Ikeda, Y Sawaki

Index: Ishiguro, Katsuya; Ikeda, Masatoshi; Sawaki, Yasuhiko Journal of Organic Chemistry, 1992 , vol. 57, # 11 p. 3057 - 3066

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Citation Number: 21

Abstract

One-electron oxidation of phenyldiazomethanes afforded cis-stilbene predominantly. The reaction was independent of the oxidation methods, eg, electrolysis, copper (II), triarylaminium salts, or photosensitized one-electron oxidations. The CC coupling reaction was retarded by introducing a-substituents on phenyldiazomethane. The ESR spectra of diazoalkane radical cations could be obtained during the electrolysis at low temperature ...

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