Mechanism of cyclopentene-1-carboxaldehyde formation by ring contraction of 2, 3-epoxycyclohexanols. Improved synthetic procedures

R Bergman, G Magnusson

Index: Bergman, Rolf; Magnusson, Goeran Journal of Organic Chemistry, 1986 , vol. 51, # 2 p. 212 - 217

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Citation Number: 20

Abstract

Complete analysis of the reaction mixtures from lithium bromide induced skeletal rearrangement of cis-and trans-l-deuteric-4, 4-dimethyl-2, 3-epoxycyclohexanol (4d and 7d) showed that the formation of specifically deuterated 5, 5-and 3, 3-dimethylcyclopentene-l- carboxaldehydes (Id, 2d, and 2) occurred by a route that requires the participation of practically all possible configurational and conformational halohydrin intermediates. Small ...