Reaction of 1,4,2-dithiazolium and 1,3-dithiolium salts with malononitrile.
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概要
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The reaction of 5-substituted 3-phenyl-1,4,2-dithiazolium salts with malononitrile gave not only 5-dicyanomethylene-3-phenyl-1,4,2-dithiazole and an isothiazole derivative, but 4-amino-5-cyano-2-(1-cyano-2-dialkylamino-2-mercaptovinyl)-6-phenylpyrimidines (<B>6</B>) and a butadiene derivative, depending on substituents at C-5 and bases used. The structure of <B>6</B> was confirmed by X-ray crystallographic analysis of its methylated derivative. These results are well explained by assuming three possible fission modes of the initial adduct: liberation of substituents at C-5 (Path A), ring opening-ring closure reaction (Path B), and fragmentation of dithiazole ring (Path C). On the other hand, 2-dialkylamino-4,5-diphenyl-1,3-dithiolium salts were allowed to react with malononitrile to afford 2-amino-3-cyano-5,6-diphenyl-1,4-dithiin (<B>13</B>) and 4-amino-3-cyano-2-dicyanomethylene-5,6-diphenyl-2<I>H</I>-thiin (<B>14</B>) as well as 2-dicyanomethylene-4,5-diphenyl-1,3-dithiole (<B>12</B>). In a separate experiment, both <B>13</B> and <B>14</B> were formed by the reaction of <B>12</B> with malononitrile. This pathway can be interpreted in terms of considerable contribution of polar structure of <B>12</B> due to the push–pull effect of sulfur atoms and cyano groups. Furthermore, the reaction of 2-substituted 4-phenyl-1,3-dithiolium salts with malononitrile also gave 2-dicyanomethylene-4-phenyl-1,3-dithiole and thiophene derivatives.
- 公益社団法人 日本化学会の論文
著者
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Shibuya Isao
National Institute Of Advanced Industrial Science And Technology(aist) Tsukuba Central 5
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Honda Kazumasa
National Chemical Laboratory for Industry
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Yonemoto Katsumi
National Chemical Laboratory for Industry
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Shibuya Isao
National Chemical Laboratory for Industry
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