Synthesis 2003(1): 0045-0048
DOI: 10.1055/s-2003-36250
PAPER
© Georg Thieme Verlag Stuttgart · New York

Trichloroisocyanuric Acid as a Cohalogenating Reagent: An Efficient Transformation of Alkenes into Chlorohydrins, β-Chloroethers and β-Chloroacetates

Gabriela Fonseca Mendonça, Antonio Manzolillo Sanseverino, 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;
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Publikationsverlauf

Received 29 May 2002
Publikationsdatum:
18. Dezember 2002 (online)

Abstract

The preparation of diverse β-chloroethers, β-chloroacetates, and chlorohydrins is efficiently achieved under mild conditions by reaction of alkenes with trichloroisocyanuric acid (0.34 mol equiv) in alcohols (MeOH, EtOH, i-PrOH, t-BuOH), acetic acid or aqueous acetone, respectively.