Organic letters

Catalysis of phosphorus (V)-mediated transformations: dichlorination reactions of epoxides under Appel conditions

RM Denton, X Tang, A Przeslak

Index: Denton, Ross M.; Tang, Xiaoping; Przeslak, Adam Organic Letters, 2010 , vol. 12, # 20 p. 4678 - 4681

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Citation Number: 43

Abstract

A stereospecific triphenylphosphine oxide-catalyzed 1, 2-dichlorination reaction of epoxides has been developed. The reaction 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.