The addition of thiols to 5,6-dimethylenenorborn-2-ene, and its reactivity towards thiol addition relative to the reactivity of other bridged polycyclic olefins

Abstract

The products formed on the addition of thiophenol to 5,6-dimethylenenorborn-2-ene have been identified by means of nuclear magnetic resonance spectroscopy, and possible pathways of product formation are discussed. The addition of p-thiocresol and methanethiol is briefly reported. The relative reactivities of 5,6-dimethylenenorborn-2-ene and various other bridged polycyclic olefins towards reaction with (a) thiophenol and (b) methyl mercaptoacetate have been determined, and the significance of the results reviewed.