Tetrahedron

Bromine–magnesium exchange in gem-dibromocyclopropanes using Grignard reagents

MS Baird, AV Nizovtsev, IG Bolesov

Index: Baird, Mark S; Nizovtsev, Alexey V; Bolesov, Ivan G Tetrahedron, 2002 , vol. 58, # 8 p. 1581 - 1593

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Citation Number: 37

Abstract

Reaction of gem-dibromocyclopropanes with ethylmagnesium bromide at ambient temperature leads to very high yields of allenes; when cyclopropylidene–allene ring opening is suppressed, alternative carbenic products are observed, although other reactions compete. When the reactions are carried out at− 60° C, a 1-bromo-1-(bromomagnesio)- cyclopropane is formed which may be trapped by a number of electrophiles.