Reactions of m-chloroperbenzoic acid with olefins which have neighbouring functional groups

Abstract

The reaction of trans-stilbene-2-carboxylic acid with m-chloroperbenzoic acid yields trans-3,4-dihydro-4-hydroxy-3-phenylisocoumarin. The epoxide of trans-stilbene-2-carboxylic acid was detected as an intermediate by n.m.r. spectroscopy. The rates of reactions of pent-4-en-1-ol and hex-5-en-1-ol with m-chloroperbenzoic acid are similar to that of hex-1-ene, and that of o-allylphenol is about twice as great as that of o-ailylbenzene. It was concluded that these reactions also involved initial formation of an epoxide.