Manganese (III). gamma.-lactone annulation with substituted acids

WE Fristad, JR Peterson, AB Ernst

Index: Fristad, William E.; Peterson, John R.; Ernst, Andreas B. Journal of Organic Chemistry, 1985 , vol. 50, # 17 p. 3143 - 3148

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Citation Number: 80

Abstract

Manganese (II1) acetate oxidation of several HOOCCH2X, X= electron withdrawing group, in the presence of alkenes led to the formation of a-substituted y-lactones. Chloroacetic acid gave a-chloro y-lactones, which were converted in two steps to the corresponding a,@- unsaturated y-lactones. 3-Chloropropanoic acid led to the a-methylene y-lactone after base induced elimination of HC1. Cyanoacetic acid produced a-cyano y-lactones which could ...