SOME NOVEL SULFONAMIDES - CHLOROSULFONATION OF ARYL ALKYL SULFIDES

被引:3
作者
GOLDKAMP, AH
机构
[1] Chemical Research Division, G. D. Searle & Co., Chicago
关键词
D O I
10.1021/jo01258a056
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chlorosulfonation of three methylthio-substituted benzenes has been investigated. With two of the compounds, the reaction proved satisfactory for preparation of sulfonamide derivatives. In the more favorable case, 2,4-dimethylthioacetanilide readily gave a crystalline sulfonyl chloride. Subsequent oxidation gave the corresponding disulfones. Various tetrasubstituted compounds were readily characterized by bands for isolated aromatic hydrogens in their proton magnetic resonance (pmr) spectra. Lack of splitting in these bands along with the facile substitution in the presence of the two methylthio-directing groups favors assignment of a 1,2,4,5-substitution pattern for these compounds. Analysis of the pmr spectra provides a rough correlation of chemical-shift parameters for the sulfonyl and methylthio substituents. © 1969, American Chemical Society. All rights reserved.
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页码:1780 / &
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