Rearrangements of ethylene oxide derivatives. Stereoselectivity of the prochiral C1 hydrogens in the boron trifluoride catalysed rearrangement of 1, 2- …

JM Coxon, C Lim

Index: Coxon,J.M.; Lim,C.-E. Australian Journal of Chemistry, 1977 , vol. 30, p. 1137 - 1143

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Citation Number: 19

Abstract

Abstract The boron trifluoride catalysed rearrangement of 1,2-epoxyoctane to give octanal proceeds by selective (c. 1.4 : 1) migration of the prochiral hydrogen trans to the alkyl group. ... Introduction The intermediacy of carbonium ions is now well established1-4 for acid-catalysed rearrangements where the epoxide contains a tertiary carbon. The mechanism of intramolecular acid-catalysed reactions of epoxides which do not contain tertiary epoxide carbons is however less well ...