Bromochlorination of alkenes with dichlorobromate(1-) ion. V Regio- and stereochemistry for the bromochlorination of styrene derivatives with dichlorobromate(1-) ion in protic solvents.

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概要

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• The bromochlorination of styrene derivatives with tetrabutylammonium dichlorobromate(1−) (<B>1</B>) in such protic solvents as acetic acid and methanol gives the corresponding bromo chloro adducts along with substantial amounts of solvent-incorporated products in a regiospecific manner (regioselective in the case of 3-nitro- or 2-chlorostyrenes). The reaction of 1-phenylpropenes with <B>1</B> gives nonstereospecific but regiospecific adducts. These results suggest that the addition of <B>1</B> to styrene derivatives in protic solvents involves an attack of chloride ion or solvent molecule to a bromonium ion intermediate.

• 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

• Regio- and stereochemistry of bromochlorinations of alkynes with molecular bromine chloride and dichlorobromate(1-) ion.
• Bromochlorination of alkenes with dichlorobromate(1-) ion. II. Regio- and stereochemistry for the bromochlorination of 1-phenylpropenes with dichlorobromate(1-) ion.
• Bromochlorination of alkenes with dichlorobromate(1-) ion. V Regio- and stereochemistry for the bromochlorination of styrene derivatives with dichlorobromate(1-) ion in protic solvents.
• Bromochlorination of alkenes with dichlorobromate(1-) ion. IV Regiochemistry of bromochlorinations of alkenes with molecular bromine chloride and dichlorobromate(1-) ion.
• The sulfuranyl radical structure and reactions of o-(thio)benzoyloxyl radicals formed by the decomposition of t-butyl o-(thio)-perbenzoates studied by 1H and 13C CIDNP and 17O NMR.
• Substituent effects in the ionization of trans-2-substituted cyclopropanecarboxylic acids.
• The Estimation of the Electronic Effects of Cyclopropyl and 2,2-Dichlorocyclopropyl Groups

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