Dimethylformamide, dimethylacetamide and tetramethylguanidine as nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
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Ahmad, Simon M.
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机构:Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
Ahmad, Simon M.
Braddock, D. Christopher
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Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, EnglandUniv London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
Braddock, D. Christopher
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Cansell, Gemma
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机构:Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
Cansell, Gemma
Hermitage, Stephen A.
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机构:Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
Hermitage, Stephen A.
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[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] GlaxoSmithKline Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
Dimethylformamide, dimethylacetamide and tetramethylguanidine were found to act as increasingly active catalysts for the bromolactonisation of gamma,delta- and delta,epsilon-unsaturated carboxylic acids with N-bromosuccinimide. The catalysts are readily removed in the work-up by washing with water to provide the pure bromolactone products without the need for column chromatography. Catalysis of the intermolecular bromoacetoxylation of alkenes with acetic acid and NBS by TMG was also demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.