Tetrahedron

An unusual reaction between the esters of N-hydroxy-2-thiopyridone and activated azo compounds

DHR Barton, N Ozbalik, B Vacher

Index: Barton, Derek H. R.; Ozbalik, Nubar; Vacher, Bernard Tetrahedron, 1988 , vol. 44, # 24 p. 7385 - 7392

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Citation Number: 22

Abstract

The esters 1 of N-hydroxy-2-thiopyridone react smoothly at room temperature in a thermal reaction with diethyl azodicarboxylic ester to furnish adducts 2 of a novel structure. Photolysis of these adducts affords a convenient route to the little known tetrazanes 8. Azo compounds without electron withdrawing groups do not react. The Cookson reagent, however, is so reactive that it gives diacyl derivatives of type 14.