Abstract
Abstract The chlorination of norbornene and cyclooctadienes with sulfuryl chloride and phosphorus(V) chloride has been investigated mainly in carbon tetrachloride under various conditions. From the studies of the product distributions and the effect of radical scavengers, the following facts have been revealed for the first time in olefin chlorination: chlorination with sulfuryl chloride proceeds through an ionic pathway at room temperature or in the presence of silica gel and that with phosphorus(V) chloride through a radical pathway at elevated temperature, and an ionic chlorination with phosphorus(V) chloride in nonpolar solvents does not seem to involve C–P bond formation through the reaction.
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