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Trihaloisocyanuric Acid/Triphenylphosphine: An Efficient System for Regioselective Conversion of Epoxides into Vicinal Halohydrins and Vicinal Dihalides under Mild Conditions

Vitor S. C. de Andrade, Marcio C. S. de Mattos*

*Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68545, Rio de Janeiro CEP 21945-970, Brazil, Email: mmattosiq.ufrj.br

V. S. C. de Andrade, M. C. S. de Mattos, Synthesis, 2016, 48, 1381-1388.

DOI: 10.1055/s-0035-1560408 (free Supporting Information)


 
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Abstract

The use of trihaloisocyanuric acid/triphenylphosphine enables a regioselective conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides under mild and neutral conditions in acetonitrile. The reactions proceed smoothly in high yield at room temperature and at reflux, respectively, over a short time.

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Key Words

dihalides, epoxide, chlorohydrins, bromohydrins, TCCA, TBCA, halogenation, N-halo reagent


ID: J66-Y2016