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 thienylketofuranoses 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.

Thiazole as leaving group. Thermal elimination from thiazolylketoses

DONDONI, Alessandro;MARRA, Alberto
1999

Abstract

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 thienylketofuranoses 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.
1999
Dondoni, Alessandro; Marra, Alberto
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1201437
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