T. Negoro, Y. Ikeda
Aug 1, 1984
Citations
0
Influential Citations
17
Citations
Journal
Bulletin of the Chemical Society of Japan
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.