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■ 8H-Anhydro-4-hydroxy-2-oxo-1,3-thiazinium Hydroxides as Mesoionic 1,4-Dipoles

Albert Padwa,* Steven J. Coats, and Lazaros Hadjarapoglou

*Department of Chemistry, Emory University, 1515 Pierce Drive Atlanta, Georgia 30322, U.S.A.

Abstract

The previously unknown 8H-anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides (1) were prepared and their 1,4-dipolar cycloaddition behavior was examined. In most cases, elimination of the proton in the 8-position of the mesoionic ring was observed to occur unless extremely reactive dipolarophiles were used. The S,N-ketene acetals were converted to the corresponding α-diazo ketones for further study.