The Journal of Organic Chemistry

Addition of hydrogen bromide to 1-trimethylsilyl-1-alkynes. Convenient synthesis of 2-bromo-1-alkenes

RK Boeckman Jr, DM Blum

Index: Boeckman,R.K.; Blum,D.M. Journal of Organic Chemistry, 1974 , vol. 39, p. 3307 - 3308

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Citation Number: 17

Abstract

Summary: The reaction of anhydrous HBr with terminal trimethylsilylalkynes is a rapid free- radical reaction resulting in the elimination of the trimethylsilyl group as the halide and the production of 2-bromo-1-alkenes in high yield; a series of alkynes were studied and some mechanistic details elucidated; the method represents a significant improvement in the synthesis of 2-bromo-1-olcfins over existing literature methods.