Epoxidation of substituted norbornenes. Stereochemical aspects and accompanying intramolecular transformations

Abstract

Traditional and new procedures for epoxidation of substituted norbornenes are described. The stereochemistry of this reaction and the influence of substituents on the reactivity of the substrate are analysed. The molecular rearrangements and heterocyclisation reactions that can accompany epoxidation are considered; examples of selective attack of oxidants at one of the double bonds in norbornenes containing an unsaturated substituent and also at a multiple bond in some polycyclic di- and triene systems are given. The bibliography includes 252 references.