The Journal of Organic Chemistry

Dipole-stabilized carbanions from thioesters. Secondary. alpha.'-lithiocarbamates and tertiary. alpha.'-lithio thioesters

P Beak, PD Becker

Index: Beak, Peter; Becker, Peter D. Journal of Organic Chemistry, 1982 , vol. 47, # 20 p. 3855 - 3861

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Citation Number: 22

Abstract

The formations of 5 and 17, synthetic equivalents of the a-lithioalkylthio and a- lithiodialkylthio functions, respectively, by deprotonations of the corresponding carbamate 4 and thioester 16 are reported. The reactions of these formally dipole-stabilized carbanions with a variety of electrophiles and their use in syntheses of 2, 3-substituted thiiranes are demonstrated. The rearrangement of 17 to an a-thiol ketone is shown to be intramolecular ...