Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Chlorination of Norbornene and Cyclooctadienes with Sulfuryl Chloride and Phosphorus(V) Chloride. Ionic vs. Radical Chlorination with Each Reagent
Sakae UemuraHajime OkazakiAkira OnoeMasaya Okano
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1978 Volume 51 Issue 12 Pages 3568-3570

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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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