Synthesis of Arylethylenesulfonamides and Intramolecular Rearrangement of<i>N</i>-(Arylethylenesulfonyl)thioureas
作者:Kiyoshi Hasegawa、Syuzi Hirooka、Tadashi Sasaki
DOI:10.1246/bcsj.48.1513
日期:1975.5
onyty)-N′-alkylthioureas (12) with bases afforded new intramolecularly rearranged N-alkyl-S-(2,2-diarylvinyl)- (13), N-alkyl-S-[2-phenyl-2-(α-naphthyl)vinyl]- (14), and N-alkyl-S-(p-nitrostyryl)isothioureas (15), respectively, p- and p′-Substituted 2,2-diarylethylene-N-methylsulfonamides (6) were treated with carbon disulfide and alkyl halides in the presence of a base to give alkyl 2,2-diarylvinyl
p-和p'-取代的N-(2,2-二芳基亚乙基磺酰基)-(8)、N-[2-苯基-2-(α-萘基)亚乙基磺酰基]-(9)和N-(p -硝基苯乙烯-1-磺酰基)-N'-烷基硫脲 (12) 与碱提供新的分子内重排 N-烷基-S-(2,2-二芳基乙烯基)- (13), N-烷基-S-[2-苯基- 2-(α-萘基)乙烯基]-(14)和N-烷基-S-(对硝基苯乙烯基)异硫脲(15),分别是对-和对'-取代的2,2-二芳基乙烯-N-甲基磺酰胺( 6) 在碱存在下用二硫化碳和烷基卤化物处理,得到烷基 2,2-二芳基乙烯基三硫代碳酸酯 (17)。磺酰硫脲和-酰胺的反应性顺序表明苯环上的电子释放对位取代基(Cl>H>CH3>OCH3)阻碍了重排。