Tri(hetero)substituted Carbonium Ions. IV. Reactions of <I>N</I>,<I>N</I>′-Dimethyl-<I>S</I>,<I>S</I>′-dimethyldithiocarbamidium Ion with Various Nucleophiles
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概要
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A wide spectrum of electrophilic reactivity has been shown by <I>N</I>,<I>N</I>-dimethyl-<I>S</I>,<I>S</I>′-dimethyldithiocarbamidium perchlorate (II). Results obtained reveal that II behaves toward nucleophiles as an ambident electrophile with two reactive sites, a centered electron-definicent carbon and <I>S</I>-methyl carbon atom. The electrophilic behavior of II has been compared with that of a cyclic analog, 2-dimethylamino-1,3-dithiolanylium ion, and of a sulfur analog, tris (methylthio)-carbonium ion. Attempts to utilize II for synthetic reactions were made. Reactions of II with active methylene compounds gave ketone <I>N</I>,<I>S</I>-acetals which are of great interest from the standpoint of structural chemistry. <I>o</I>-Phenylenediamine and <I>o</I>-aminophenol reacted with II to give 2-dimethylamino-benzimidazole and -benzoxazole, respectively, in good yields. The reactions may provide a new method of introducing 2-dialkylamino groups into these heterocycles. Reactions of II with two equivalents of primary amines afforded tetrasubstituted guanidines. Reactions of II with <I>p</I>-toluenesulfonylhydrazine and an enamine were also studied.
- 公益社団法人 日本化学会の論文
著者
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Okawara Makoto
Research Laboratory Of Resources Utilization Tokyo Institute Of Technology
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Nakai Takeshi
Research Laboratory of Resources Utilization, Tokyo Institute of Technology
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