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Synthesis 2010(14): 2379-2382  
DOI: 10.1055/s-0029-1220011
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Halofluorination of Alkenes Using Trihaloisocyanuric Acids and HF×Pyridine

Lívia T. C. Crespo, Rodrigo da S. Ribeiro, Marcio C. S. de Mattos*, Pierre M. Esteves*
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)25627256; e-Mail: pesteves@iq.ufrj.br; e-Mail: mmattos@iq.ufrj.br;
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Publikationsverlauf

Received 29 January 2010
Publikationsdatum:
18. Mai 2010 (online)

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Abstract

Halofluorination of alkenes with a new system (trihaloisocyanuric acids and HF˙pyridine) results in the formation of vicinal halofluoroalkanes. The reaction is regioselective leading to Markovnikov-oriented products and the halofluorinated adducts follow anti-addition in the case of cyclohexene and 1-methylcyclohexene. Reaction yields range from 67-88%.

Key words

electrophilic addition - halogenation - alkenes - halides - regioselectivity

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