Chemistry Letters

Diazomethane radical cations as a dipolarophile in the dimeric olefin formation from diazo-compounds.

K Ishiguro, Y Sawaki, H Iwamura

Index: Ishiguro, Katsuya; Sawaki, Yasuhiko; Iwamura, Hiizu Chemistry Letters, 1987 , p. 1853 - 1856

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Abstract

A novel cycloaddition mechanism involving diazomethane radical cations is proposed for the dimeric olefin formation by the one-electron oxidation of diazo-compounds. The preference of cis-stilbene formation from phenyldiazomethane is understood by a secondary orbital interaction of phenyl groups on the cycloaddition step.