The photochlorination of butyryl and valeryl chloride: (Preliminary communication)

Abstract

AbstractSome preliminary experiments on the photochlorination of butyryl and valeryl chloride in the liquid and the vapour phase are described.The chlorination of butyryl chloride in the liquid phase yields about equal quantities of β‐ and γ‐chlorobutyryl chloride and only a small amount of the α‐chloro compound. In the gas phase somewhat more of the β‐chloro derivative is formed.In the chlorination of valeryl chloride, too, the substitution preferentially occurs in positions remote from the carbochloride group. This result differs considerably from that obtained by Bruylants and collaborators'). These authors report that in the gas phase, together with a small amount of the a‐chloro compound, only β‐ and γ‐chlorovaleryl chloride are formed, whereas we have found that the reaction mixture contains, in addition to the above‐mentioned substances, 25‐30% of δ‐chlorovaleryl chloride. Our results do not support the hypothesis of Bruylants c.s. that the course of the chlorination depends on a cyclic conformation of the acid halides.