The Wittig-type reaction of O=C-, C=C-, and N=C-substituted methylenetriphenylphosphoranes with N-sulfinyl-p-toluenesulfonamide. An intramolecular 1,3-dipolar cyclization of imidoyl-conjugated thione S-imides.
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概要
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The Wittig-type reactions of <I>N</I>-sulfinyl-<I>p</I>-toluenesulfonamide with (1) O=C–, (2) C=C–, and (3) N=C-conjugated phosphorus ylides were investigated. In the reaction with (1), <I>N</I>-sulfinyl-<I>p</I>-toluenesulfonamide reacted at both the ylide and the carbonyl moiety to form TsN=C-conjugated thione <I>S</I>-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 <I>S</I>-imides.
- 公益社団法人 日本化学会の論文
著者
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KOBAYASHI Kimiko
The Institute of Physical and Chemical Research
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SAKURAI Tosio
The Institute of Physical and Chemical Research
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Motoki Shinichi
Department Of Chemistry Faculty Of Science Science University Of Tokyo
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Watanabe Toshihiko
Department Of Aeronautics And Astronautics University Of Tokyo
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Saito Takao
Department Of Biochemistry And Surgery Oita Medical School
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Watanabe Toshihiko
Department of Chemistry, Faculty of Science, Science University of Tokyo
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Nakane Michio
Department of Chemistry, Faculty of Science, Science University of Tokyo
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