Regio- and stereochemistry of bromochlorinations of alkynes with molecular bromine chloride and dichlorobromate(1-) ion.

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概要

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• The bromochlorination of phenyl- and alkyl-substituted acetylenes with tetrabutylammonium dichlorobromate(1−) (<B>1</B>) in dichloromethane was found to be <I>anti</I>-stereospecific and nonregiospecific (regiospecific in the case of phenylacetylene). Whereas the addition of molecular bromine chloride (<B>2</B>) to phenyl-substituted acetylenes was found to give nonstereospecific and regiospecific adducts, the reaction of alkyl-substituted acetylenes gave <I>anti</I>-stereospecific and nonregiospecific adducts. These results suggest that the addition of <B>1</B> involves an attack of chloride ion to a three-centered π-complex in the product-forming stage, and that the addition of <B>2</B> to phenyl-substituted acetylenes involves a vinyl cation intermediate (but a bridged bromonium ion intermediate in the case of alkyl-substituted acetylenes).

• 公益社団法人 日本化学会の論文

著者

• Negoro Takeshi

  Department of Chemistry, Faculty of Education, Wakayama University

• Ikeda Yoshitsugu

  Department of Chemistry, Faculty of Education, Wakayama University

関連論文

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