Stereoselectivity in the synthesis of enol esters from chloromercurio aldehydes and acyl chlorides.

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概要

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• Reactions of chloromercurio aldehydes with acyl chlorides gave a variety of (<I>Z</I>)- and (<I>E</I>)-enol esters. The <I>Z</I>/<I>E</I> ratio of the enol esters is dependent on the structure of chloromercurio aldehydes but independent of that of acyl chlorides. <I>Z</I>-Rich enol esters were prepared by acylation of 2-chloromercurio aldehydes derived from propanal, butanal, and 2-phenylethanal, while <I>E</I>-rich 1-acyloxy-1,3-butadiene was obtained by acylation of (<I>E</I>)-4-chloromercurio-2-butenal. Reaction mechanisms for the stereoselective formation of these enol esters are discussed together with the isomer composition of starting enol acetates from which the chloromercurio aldehydes were prepared.

• 公益社団法人 日本化学会の論文

著者

• Kakiuchi Hiroshi

  Department Of Applied Chemistry Faculty Of Engineering Yokohama National University

• Fukuda Wakichi

  Department of Chemical Industry, Faculty of Engineering, Yokohama National University

• Sato Hozumi

  Department of Applied Chemistry, Faculty of Engineering, Yokohama National University

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• Stereoselectivity in the synthesis of enol esters from chloromercurio aldehydes and acyl chlorides.

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