Bulletin of the Chemical Society of Japan p. 2882 - 2888 (1985)
Update date:2022-08-05
Topics:
Saito, Takao
Nakane, Michio
Watanabe, Toshihiko
Motoki, Shinichi
Kobayashi, Kimiko
Sakurai, Tosio
The Wittig-type reactions of N-sulfinyl-p-toluenesulfonamide with (1) O=C-, (2) C=C-, and (3) N=C-cojugated phosphorus ylides were investigated.In the reaction with (1), N-sulfinyl-p-toluenesulfonamide reacted at both the ylide and the carbonyl moiety to form TsN=C-conjugated thione S-imide, which underwent intramolecular 1,3-dipolar cycloaddition of the CSN group with the aromatic C=C bond of the tosyl group giving a structurally unique spiro-fused tricyclic adduct.The structure of the adduct was determined by means of X-ray diffraction.In the reactions with (2) and (3), 1-azadiene and sulfobetaines were obtained instead of the expected conjugated thione S-imides.
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