The reactivities of phenyl benzenethiosulfonate, o-nitrophenyl benzenethiosulfonate and 1, 2-bis (benzenesulfonylthio) ethane toward several active methylene compounds were examined. Consequently, bis (phenylmercapto) malondiamide obtained by the reaction of phenyl benzenethiosulfonate with malondiamide at room temperature was found to eliminate readily one of carboxamide and phenylmercapto group by warming at the temperature above 35°. On the other hand, bis (phenylmercapto) malonate was similarly eliminated one of phenylmercapto group under the same condition, without elimination of carboxylate group. 1-Benzylmercapto-1-phenylmercaptomalondiamide and 1-ethyl-1-phenylmercaptomalondiamide were eliminated one of carboxamide group, without elimination of any mercapto group. Moreover, 1, 2-bis (benzenesulfonylthio) ethane was allowed to react with malondiamide and acetylacetone to give cyclic compound, ethylenedithiomalondiamide and ethylenedithioacetylacetone, respectively. With comparison of these reactions, the reaction of benzyl benzenesulfonate with cyanoacetamide was carried out to result in the benzylation of cyanoacetamide.
对苯基苯
硫磺酸盐、邻
硝基苯基苯
硫磺酸盐和1,2-双(苯磺酰
硫)
乙烷与几种活性亚甲基化合物的反应性进行了研究。因此,在室温下,苯基苯
硫磺酸盐与
氨基二
甲酸反应得到的双(苯基
硫代)
氨基二
甲酸发现可以在高于35°C的温度下迅速消除其中一个
氨基和苯基
硫代基。另一方面,双(苯基
硫代)
马来酸在相同条件下也消除了其中一个苯基
硫代基,但未消除
羧酸根基。1-苯基
硫代-1-苯基
硫代
氨基二
甲酸和1-乙基-1-苯基
硫代
氨基二
甲酸则消除了其中一个羧酰胺基,而没有消除任何
硫代基。此外,1,2-双(苯
硫酰
硫)
乙烷与
氨基二
甲酸和乙酰乙酮反应,分别得到环状化合物
乙烯二
硫亚
氨基二
甲酸和
乙烯二
硫乙酰乙酮。通过比较这些反应,还进行了苄基
苯磺酸盐与
氰乙酸酰胺的反应,结果导致了
氰乙酸酰胺的苄基化。