THIAZOLE AS LEAVING GROUP.THERMAL ELIMINATION FROM THIAZOLYLKETOSES

摘要

Heating thiazolylketofuranoses and -ketopyranoses in refluxing toluene results in the elimination of thiazole and formation of the corresponding sugar lactones in nearly quantitative yield.The same reaction does not occur with 1-O-acetyl and 1-O-trimethylsilyl derivatives.Also model furyl-and thienyl-ketofuranoses and various thiazolyl alcohols proved to be stable under the above thermolysis conditions.A possible mechanism of the observed thermolysis of thiazolylketoses involves the thiazolium 2-ylide as the actual leaving group.