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Catalysis of Phosphorus(V)-Mediated Transformations: Dichlorination Reactions of Epoxides Under Appel Conditions

Ross M. Denton*, Xiaoping Tang and Adam Przeslak

*School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, United Kingdom, Email: ross.dentonnottingham.ac.uk

R. M. Denton, X. Tang, A. Przeslak, Org. Lett., 2010, 12, 4678-4681.

DOI: 10.1021/ol102010h (free Supporting Information)


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Abstract

A stereospecific triphenylphosphine oxide-catalyzed 1,2-dichlorination reaction of epoxides is effective for a range of terminal and internal epoxides. In contrast to the classical Appel-type dichlorination of epoxides, oxalyl chloride is used as a stoichiometric reagent to generate the chlorophosphonium salt responsible for dichlorination from catalytic triphenylphosphine oxide.

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proposed catalytic cycle



Key Words

1,2-dichloroalkanes, Appel Reaction


ID: J54-Y2010-2940