I. B. Rozentsveig, Yu. A. Aizina, K. A. Chernyshev
May 1, 2007
Citations
1
Influential Citations
2
Citations
Journal
Russian Journal of General Chemistry
Abstract
The mixtures of mono-and dihalothiophenesulfonyl chlorides, formed in the sulfochlorination reaction of 2,5-dichlorothiophene and 2,5-dibromothiophene, were treated with aqueous ammonia and thus converted into mixtures of the corresponding stable thiophenesulfonamides. The structure and composition of the latter were studied by physicochemical methods: GC-MS and 1H, 13C, 1H-13C HSQC, 1H-13C HMBC, and NOESY NMR spectroscopy. As a result of the above chemical transformations, 2,5-dichlorothiophene afforded a mixture of 5-chlorothiophene-2-sulfonamide and 4,5-dichlorothiophene-3-sulfonamide in a roughly 70:30 ratio. In the case of 2,5-dibromothiophene, a mixture of 5-bromothiophene-2-sulfonamide, 4,5-dibromothiophene-3-sulfonamide, and 3,5-dibromothiophene-2-sulfonamide (3:54:43) was formed.