Bromination of alkenes and alkynes with (bromodimethyl) sulfonium bromide

B Das, Y Srinivas, C Sudhakar…

Index: Das, Biswanath; Srinivas, Yallamalla; Sudhakar, Chittaluri; Ravikanth, Bommena Journal of Chemical Research, 2008 , # 4 p. 188 - 190

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Citation Number: 9

Abstract

Alkenes and alkynes were brominated efficiently in high yields with (bromodimethyl) sulfonium bromide in acetonitrile at room temperature. Alkenes produced the corresponding trans-dibromo compounds while alkynes (except phenylacetylene) afforded both the trans- dibromo products (major) and the tetrabromo derivatives (minor). However, phenylacetylene furnished solely the tetrabromo compound.

 Related Synthetic Route
Phenylacetylene Structure

536-74-3

Phenylacetylene

~95%

Benzene,(1,1,2,2-tetrabromoethyl)- Structure

31253-21-1

Benzene,(1,1,2,...

Hex-1-yne Structure

693-02-7

Hex-1-yne

~61%

1,2-dibromohex-1-ene Structure

49677-13-6

1,2-dibromohex-1-ene

N/A Structure

49677-15-8

N/A

4-Methylstyrene Structure

622-97-9

4-Methylstyrene

~95%

1-(1,2-dibromoethyl)-4-methylbenzene Structure

33458-08-1

1-(1,2-dibromoe...


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