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

1984; Oxford University Press; Volume: 57; Issue: 8 Linguagem: Inglês

10.1246/bcsj.57.2116

1348-0634

Takeshi Negoro, Yoshitsugu Ikeda,

Inorganic and Organometallic Chemistry

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 of bromine chloride in the form of (n-C4H9)4NBrCl2 involves a rate- and product-determining attack of a chloride ion to a three-center bound π complex.