ORGANIC HETEROCYCLOTHIAZENES .18. 1,3,2-DITHIAZOLIUM SALTS AND 1,3,2-DITHIAZOLETHIONES

被引:9
作者
GRAY, MA
REES, CW
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 24期
关键词
D O I
10.1039/p19930003077
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,3,2-Dithiazol-1 -ium chloride 6 and 5-chloro-1,3,2-dithiazol-1 -ium chloride 7 have been prepared by the reaction of trimethylsilyl azide with 1-chloroethane-1,2-bis(sulfenyl chloride) and 1,2-dichloroethane-1,2-bis(sulfenyl chloride) respectively. The corresponding neutral 1-lambda4delta2,3,2-dithiazole-4-thione 8 and 5-chloro-1-lambda4delta2,3,2-dithiazole-4-thione 18 were unexpectedly obtained by treatment of these salts with base. Methylation and benzylation of the thione 8 provided the 5-methylthio-1,3,2-dithiazol-1-ium 9 and 4-benzylthio-1,3,2-dithiazol-1-ium 12 salts, which on treatment with base afforded 5-methylthio- 10 and 5-benzylthio-1-lambda4delta2,3,2-dithiazole-4-thione 13 respectively; further alkylation provided a route to symmetrical difunctionalised cations such as 4,5-dimethylthio-1,3,2-dithiazol-1-ium iodide 11. Treatment of the dithiazolium chloride 7 with ammonia or aniline leads to 5-amino- 19 and 5-anilino-1-lambda4delta2,3,2-dithiazole-4-thione 20 respectively.
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页码:3077 / 3080
页数:4
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