Bromochlorination of alkenes with dichlorobromate(1-) ion. II. Regio- and stereochemistry for the bromochlorination of 1-phenylpropenes with dichlorobromate(1-) ion.
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概要
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The bromochlorinations of 1-phenylpropenes with tetrabutylammonium dichlorobromate(1–) in aprotic solvents (dielectric constants 5–36) were found to be completely <I>anti</I> 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 (<I>n</I>-C<SUB>4</SUB>H<SUB>9</SUB>)<SUB>4</SUB>NBrCl<SUB>2</SUB> involves a rate- and product-determining attack of a chloride ion to a three-center bound π complex.
- 公益社団法人 日本化学会の論文
著者
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Negoro Takeshi
Department of Chemistry, Faculty of Education, Wakayama University
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Ikeda Yoshitsugu
Department of Chemistry, Faculty of Education, Wakayama University
関連論文
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