The Journal of Organic Chemistry

Stereochemistry of Carbenic 1, 2-Vinyl Shifts

W Kirmse, S Kopannia

Index: Kirmse, Wolfgang; Kopannia, Siegfried Journal of Organic Chemistry, 1998 , vol. 63, # 4 p. 1178 - 1184

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Citation Number: 10

Abstract

Various 1-phenylbut-3-enylidenes,(Ph) CCR2CH CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1, 2-Vinyl shifts, leading to 1, 3- dienes, R'CH CHC (Ph) CR2, were found to predominate over γ-CH insertion (R= Me) and to compete with 1, 2-H shifts (R= H). Intramolecular addition to the double bond was detected in the case of R= R'= Me. The resulting bicyclobutane is thermally stable and does not ...

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