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: mmattos
iq.ufrj.br
V. S. C. de Andrade, M. C. S. de Mattos, Synthesis, 2016, 48, 1381-1388.
DOI: 10.1055/s-0035-1560408
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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
