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Communication | Special issue | Vol 5, No. 1, 1976, pp.95-99
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0095
Ring Expansion of 3-Substituted 1,2-Benzoisothiazole 1,1-Dioxides to 1,2-Benzothiazepine 1,1-Dioxides

Rudolph A. Abramovitch,* Kundalika M. More, Ichiro Shinkai, and Panayencheri C. Srinivasan

*Department of Chemistry, University of Alabama, Box 870336, University, Tuscaloosa, Alabama 35478-0336, U.S.A.


3-Substituted 1,2-benzoisothiazole 1,1-dioxides undergo a [2+2] cycloaddition with 1-diethylaminopropyne followed by rinq expansion to give the very stable 5-substituted 3-diethylamino-4-methylbenzo-1,2-thiazepine 1,1-dioxides (2). These can, however, be cleaved with lithium aluminum hydride to O-styrylsulfonamides. The stability of the ring system 4 is discussed briefly.