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■ Carbenoid Rearrangements of a Cycloadduct from Phenyl Azide

Kari Skinnemoen and Kjell Undheim*

*Department of Chemistry, University of Oslo, P.O.Box 1033, Blindern, N-0315 Oslo, Norway

Abstract

Cycloaddition between phenyl azide and 2H-thiopyran-3(6H)-one is followed by isomerisation of the adduct to 5-anilino-4-diazo-4,5-dihydro-2H-thiopyran-3(6H)-one 4. On heating, 4-(anilinomethylene)-4,5-dihydrothiophen-3(2H)-one 5 and N-phenyl-2,5-dihydrothiophene-3-carboxamide 7 are formed by carbenoid rearrangements.