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

Authors

  • 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
Further Information

Publication History

Received: 04 December 2015

Accepted after revision: 18 January 2016

Publication Date:
19 February 2016 (online)


Graphical Abstract

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