Chemische Berichte

Vinylcyclobutane??cyclohexane rearrangements: zwitterions as discrete intermediates

U Gruseck, M Heuschmann

Index: Gruseck, Ursula; Heuschmann, Manfred Chemische Berichte, 1990 ,  vol. 123,  # 9  p. 1911 - 1926

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Citation Number: 3

Abstract

Abstract Donor-acceptor-substituted vinylcyclobutanes 1 rearrange to cyclohexenes 2 at temperatures between 20 and 195 C. In solvents of low polarity,[2+ 2] cycloreversion competes with ring enlargement. Under acidic conditions, addition of nucleophiles to vinylcyclobutanes 1 with ring opening is observed. Stereospecificity of rearrangement and [2+ 2] cycloreversion are functions of temperature, solvent polarity and acid catalysis. ...