1, 3-Elimination-Rearrangement of 2-Acetoxy-6-bromocyclohexanones

FG Bordwell, KM Wellman

Index: Bordwell,F.G.; Wellman,K.M. Journal of Organic Chemistry, 1966 , vol. 31, p. 351 - 357

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Citation Number: 14

Abstract

Several additional examples are given to show that the keto-enol acetates (or benzoates) formed by the reaction of cis.~ 2, 6-dibromocyclohexanones and sodium acetate arise by (a) displacement of bromine to form a cis-2-acetoxy-6-bromocyclohexanoneJ and (b) lJ3- elimination of hydrogen bromide accompanied by acyl migration. Evidence is presented to show that acyl migration does not precede loss of bromide ion. Proton magnetic ...