A study of the chlorination of some unsaturated compounds

Abstract

The products of chlorination of crotonic acid have been characterised. The reaction has been studied in a number of solvents; the reaction products are in general those expected from a conventional, heterolytic addition mechanism in which chlorine is an electrophile. Strong circumstantial evidence has been found for the formation of a-chloro-b-butyrolactone in many of the chlorination reactions investigated.The chlorination of crotonaldehyde has also been studied in a number of solvents, and its reaction products have been incompletely identified, due to experimental difficulties. A mechanism of this reaction lias been proposed.The chlorination of phenanthrene has been studied in acetic acid, and the effects of added electrolytes upon the rate and products of the reaction have been investigated. A new adauct, cis-9-acetoxy-10-chloro-dihydrophenanthrene, lias been found; to accomodate the formation of this compound, an amended reaction mechanism has been proposed.