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Communication | Regular issue | Vol 22, No. 5, 1984, pp.1025-1030
Published online, 1st January, 1970
DOI: 10.3987/R-1984-05-1025
Ring Transformation of Seven-membered Heterosyslic Sulfoxides, 2,2-Disubstituted 1,4- and 1,5-Benzothiazepine Sulfoxides

Hiroshi Shimizu, Norihiko Ueda, Tadashi Kataoka, and Mikio Hori*

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


Thermal ring transformations of 2-methyl-2-phenyl-1,4- and 1,5-benzothiazepine 1-oxides in the presence of catalytic amount of p-toluenesulfonic acid are described. trans-Sulfoxides (having methyl group cis to the sulfoxide oxygen) underwent ring expansion to afford benzothiazocine derivatives, whereas cis isomers interestingly afforded ring contraction products, indicating that the ring transformations proceeded stereospecifically.