Synthesis 2016; 48(09): 1381-1388
DOI: 10.1055/s-0035-1560408
paper
© Georg Thieme Verlag Stuttgart · New York

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
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
,
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
› Author Affiliations
Further Information

Publication History

Received: 04 December 2015

Accepted after revision: 18 January 2016

Publication Date:
19 February 2016 (online)


Abstract

A new synthetic method has been developed for the regioselective conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides by reaction with the system trihaloisocyanuric acid/tri­phenylphosphine in acetonitrile under mild and neutral conditions. The reactions proceed smoothly in high yield at room temperature and at reflux, respectively, over a short time.

Supporting Information

 
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