Regiospecificity of methylation of unsymmetrical stilbenes by methylsulphinylmethanide
作者:Brian G. James、Gerald Pattenden
DOI:10.1039/p19740001195
日期:——
gives a mixture of the stilbene (6) and the butyl sulphoxide (29), the proportion varying with the time of reaction; long periods of reaction between (21) and DMSO– give only (29). The sulphoxide (29) also results from the reaction of (6) and 2-phenyl-3-(o-tolyl)propene (36) with DMSO–. By contrast α,2-dimethylstilbene does not react further with DMSO–. The α-(α′-)methylation process by DMSO– is rationalised
的处理(ë)-2-甲基均与methylsulphinylmethanide(DMSO - )短时间产生α'的混合物,2-甲基二(6)(> 95%ë - )和3-苯基-2-(ø甲苯基)丙基亚砜(22),可从中分离出(6)(6)。收率50%。较长的反应时间得到α,2-二甲基sti [(10)+(11)]和甲基3-苯基-4-(邻甲苯基)丁基亚砜的4:5混合物(29)。(Ž)-2-甲基均给出相同的产品用DMSO -类似的条件下。Z-和E的便捷合成α,2-和α',2-二甲基对苯二酚[(6),(7),(10)和(11)]和甲基2-苯基-3-(邻甲苯基)丙基亚砜的(-)异构体( 21)和(22)的报告,以及它们与DMSO的反应的研究-进行说明。亚砜(22)与DMSO的反应-产生一个2:1混合物(10)和(11)排它地,而异构体亚砜的类似的反应(21)给出的二苯乙烯(6)和丁酯的混合物亚砜(29),其比例