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| LETTER | Synlett 2006: 1515-1518
DOI: 10.1055/s-2006-941601 |
© Georg Thieme Verlag Stuttgart · New York
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Tribromoisocyanuric Acid: A New Reagent for Regioselective Cobromination of Alkenes
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| Leonardo S. de Almeida, Pierre M. Esteves*, Marcio C. S. de Mattos* |
Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Cx. Postal 68545, 21945-970, Rio de Janeiro, Brazil
Fax: +55(21)25627133; e-Mail: mmattos@iq.ufrj.br; pesteves@iq.ufrj.br;
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Received
21 November 2006 |
Abstract
A simple one-step method for the preparation of tribromoisocyanuric acid in good yield (87%) has been developed. The reaction of tribromoisocyanuric acid with alkenes in presence of nucleophilic solvents (MeOH, i-PrOH, AcOH and a mixture of H2O-acetone, 1:5) led to the corresponding β-bromoethers, β-bromoacetates and bromohydrins, in high regioselectivity and good yields (73-98%). Key words
alkenes - cohalogenation - Oxone® - tribromoisocyanuric acid
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