Regiochemical variation in the electrophilic addition of HBr to 1-phenylprop-1-yne

The reaction of aryl alkynes with dilute methylene chloride solutions of quaternary ammonium bromide and 20% trifluoroacetic acid produces primarily the syn Markovnikov adducts of hydrogen bromide. At moderate concentrations of the bromide, the principal product is the Markovnikov anti adduct. At hi...

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Published inOrganic & biomolecular chemistry Vol. 1; no. 12; pp. 2148 - 2151
Main Authors Weiss, Hilton M, Touchette, Kim M, Andersen, Frantz, Iskhakov, David
Format Journal Article
LanguageEnglish
Published England 21.06.2003
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Summary:The reaction of aryl alkynes with dilute methylene chloride solutions of quaternary ammonium bromide and 20% trifluoroacetic acid produces primarily the syn Markovnikov adducts of hydrogen bromide. At moderate concentrations of the bromide, the principal product is the Markovnikov anti adduct. At high concentrations of bromide, the anti-Markovnikov anti addition product predominates.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/b300042g