Some free-radical addition reactions of hexachloronorbornadiene

Abstract

The free-radical addition of various thiols to hexachloronorbornadiene has been investigated and the structures of the products determined with the aid of nuclear magnetic resonance spectroscopy. A mechanism for their formation is suggested. The sulphides obtained on addition of thiophenol to hexachloronorbornadiene were oxidised to produce sulphones of differing structure with (a) hydrogen peroxide in methanol, and (b) hydrogen peroxide in acetic acid. Hexachloronorbornadiene formed an adduct with bromotrichloromethane, but not with carbon tetrachloride or chloroform. In ultraviolet light, hexachloronorbornadiene in carbon tetrachloride or chloroform solution was converted into the unusually stable hexachloroquadricyclene.