The Journal of Organic Chemistry

Lithium salt catalyzed rearrangement of epoxides. II. Glycidic esters

BC Hartman, B Rickborn

Index: Hartman,B.C.; Rickborn,B. Journal of Organic Chemistry, 1972 , vol. 37, p. 943 - 946

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Citation Number: 16

Abstract

The products 2 and 3 both arise from cleavage of the oxirane ring at the p carbon, followed by elimination or hydrogen migration. Both products could arise by a carbonium ion process, or might involve an intermediate halohydrin salt. Evidence favoring the latter mechanism in the LiBr reaction of alkyl-substituted epoxides has been presented earlier.* Attempts to further delineate this question using glycidic esters with a secondary (as opposed to ...