Bulletin of the Chemical Society of Japan

Bromochlorination of Alkenes with Dichlorobromate (1–) Ion. II. Regio-and Stereochemistry for the Bromochlorination of 1-Phenylpropenes with Dichlorobromate (1–) …

T Negoro, Y Ikeda

Index: Negoro; Ikeda Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 8 p. 2116 - 2120

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Citation Number: 20

Abstract

The bromochlorinations of 1-phenylpropenes with tetrabutylammonium dichlorobromate (1– ) in aprotic solvents (dielectric constants 5–36) were found to be completely anti stereospecific and nonregiospecific, although Markownikoff adduct was mainly formed. In marked contrast, addition of molecular bromine chloride to the same alkenes was found to give nonstereospecific and regiospecific adducts. These results suggest that the addition ...