Reactions of substituted epoxides with alkyl chloroacetate.

概要

論文の詳細を見る
The reactions of substituted epoxides with alkyl chloroacetate in the presence of lithium salts, quarternary salts and zinc chloride were studied. The reaction of 1-chloro-2,3-epoxypropane (1a) with butyl chloroacetate (BCA) in the presence of any of these catalysts yielded exclusively butyl [2-chloro-1-(chloromethyl)ethoxy]acetate (2a) via the normal cleavage of 1a followed by the reaction with the chloroacetate. On the other hand, the reaction of 1,2-epoxypropane(1b) with BCA yielded a mixture of isomeric products resulting from the normal and abnormal cleavages of 1b, and the ratio of the normal and abnormal products is dependent on the type of the catalyst. Moreover, it was found that lithium salt alone catalyzed the insertion reaction in a polar aprotic solvent, whereas the reaction in aromatic solvent needed a suitable co-catalyst such as hexamethylphosphoric triamide and triphenylphosphine oxide.
公益社団法人日本化学会の論文