The bromination of 3-arylpropynes: Evidence for phenyl participation at a vinyl cation

JA Pincock, C Somawardhana

Index: Pincock,J.A.; Somowardhana,C. Canadian Journal of Chemistry, 1978 , vol. 56, p. 1164 - 1169

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Citation Number: 11

Abstract

The bromination of substituted 3-arylpropynes in acetic acid has been examined. The only products obtained are 1, 2-dibromo-3-arylpropenes; the stereochemistry of the dibromides is predominantly trans except for the 4-methoxy isomer which gives 83% cis and 17% trans. In the presence of 0.1 M lithium bromide all substrates give predominantly trans products. Combined with rate studies, these results indicate that these acetylenes react by an ...