Tetrahedron letters

Trapping of the tribromomethylanion by electron poor alkenes

MS Baird, ME Gerrard, RJG Searle

Index: Baird, Mark S.; Gerrard, Michele E.; Searle, Robert J. G. Tetrahedron Letters, 1985 , vol. 26, # 51 p. 6353 - 6356

Full Text: HTML

Citation Number: 13

Abstract

Abstract α-Bromoacrylates, α-bromoacrylonitrile and diethyl alkylidenemalonates all react with bromoform and base under phase transfer conditions to give dibromocycloprapanes. When γ-bromine is present in a crotonate or an alkylidenemalonate, the intermediate derived by Michael addition of tribromomethylanion is trapped by cyclisation at that position to produce a (tribromomethyl) cyclopropane.