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| PAPER | Synthesis 2003: 0045-0048
DOI: 10.1055/s-2003-36250 |
© Georg Thieme Verlag Stuttgart · New York
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Trichloroisocyanuric Acid as
a Cohalogenating Reagent: An Efficient Transformation
of Alkenes into Chlorohydrins, β-Chloroethers and β-Chloroacetates
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| 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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Received
29 May 2002 |
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. Key words
alkenes - electrophilic additions - esters - ethers - halogenation
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