Stereochemical evidence for aryl participation in the ring opening of oxiranes. Ring-opening reactions of 1-benzyl-1, 2-epoxycyclohexane under acidic conditions

P Costantino, P Crotti, M Ferretti…

Index: Costantino, Paolo; Crotti, Paolo; Ferretti, Maria; Macchia, Franco Journal of Organic Chemistry, 1982 , vol. 47, # 15 p. 2917 - 2923

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Citation Number: 14

Abstract

The reactions of l-benzyl-1, 2-epoxycyclohexane (1) have been investigated and compared with the ones of the corresponding methyl-substituted oxirane (3) in order to evaluate the possibility that an aryl group not directly linked to the oxirane ring can participate in the ring- opening processes. The acid-catalyzed ring-opening reactions of 1 are not completely anti stereoselective and give mixtures of syn and anti addition products accompanied by ...