The addition of polyhalogenomethanes and related compounds to norbornadiene

Abstract

The addition of carbon tetrachloride to norbornadiene has now been shown to give endo-5-chloro-exo-3-trichloromethylnortricyclene, as well as exo-5-chloro-exo-3-trichloromethylnortricyclene as reported earlier. Bromotrichloromethane, methylene bromide, ethyl bromoacetate, and methyl bromoacetate similarly afford a mixture of two disubstituted nortricyclene isomers. In the reaction between equimolar quantities of bromotrichloromethane and norbornadiene endo-3-bromo-exo-2-trichloromethylnorborn-5-ene has been shown to constitute about 10% of the reaction product.