The Influence of the Chlorine Substituent in Some Addition Reactions of 1-Chloronorbornene

Abstract

The products of electrophilic addition of mercuric acetate, chromyl chloride and nitrosyl chloride to 1-chloronorbornene (4) have been investigated. While the rate of addition is slower than that of norbornene, the magnitude of the directive effect of the chlorine is found to vary significantly from case to case. Thus high regiospecificity is observed in oxymercuration-demercuration, moderate regiospecificity in the addition of nitrosyl chloride, and only minor preference of attachment in chromyl chloride oxidation. High stereospecificity is noted in all cases.