Construction of 1, 3-Oxathiane Ring through Pummerer Reaction of γ, δ-Unsaturated Sulfinyl Compounds

Hitoshi ABE; Hiroyuki FUJII; Chieko MASUNARI; Junko ITANI; Setsuo KASHINO; Kentaro SHIBAIKE; Takashi HARAYAMA

doi:10.1248/cpb.45.778

Hitoshi ABE, Hiroyuki FUJII, Chieko MASUNARI, Junko ITANI, Setsuo KASHINO, Kentaro SHIBAIKE, Takashi HARAYAMA

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Keywords: oxathiane, Pummerer rearrangement, p-toluenesulfonic acid, sulfinyl compound

JOURNAL FREE ACCESS

1997 Volume 45 Issue 5 Pages 778-785

DOI https://doi.org/10.1248/cpb.45.778

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Abstract

Several γ, δ-unsaturated sulfinyl compounds were prepared and their reactions with p-toluenesulfonic acid were examined. Conformationally rigid γ, δ-unsaturated sulfinyl compounds such as endo-(alkylsulfinyl)norbornene or 1-(alkylsulfinyl)-2-isopropenylbenzene derivatives afforded 1, 3-oxathianes through intramolecular Pummerer rearrangement.

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