The Reaction of 5-Substituted-2-Norbornenes with Phenylselenyl Chloride

Abstract

In dichloromethane, 5-substituted-2-norbornenes add phenylselenyl chloride across the double bond to give adducts in which the phenylselanyl substituent is exo and the chloro endo. The relative yields of the two regioisomeric adducts are reported for several of these. For most, the formation of the 2-chloro-3-phenyselanyl adduct is favoured. The main exceptions are when the 5-substituent is exo and a good resonance donor, where the 3-chloro-2-phenylselanyl adduct is the major product. Possible factors influencing the product distribution are discussed.