Methoxychlorination and dimethoxylation of alkenes the reactions of substituted styrenes with phenylselenenyl chloride in methanol
作者:Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Donatella Chianelli、Donatella Bartoli
DOI:10.1016/s0040-4020(01)81734-8
日期:1988.1
addition of PhSeCl to α- and β-substituted styrenes in methanol is regio- and stereospecific and affords the products of methoxyselenenylation. These compounds further react with PhSeCl to give the deselenenylation products. In the case of α-substituted styrenes, 1-methoxy, 2-chloroalkanes are produced, whereas with β-substituted styrenes the major reaction products are the 1,2-dimethoxyalkanes and
在甲醇中向α-和β-取代的苯乙烯中添加PhSeCl具有区域和立体特异性,并提供甲氧基硒烯化的产物。这些化合物进一步与PhSeCl反应,得到去硒烯基化产物。在α-取代的苯乙烯的情况下,产生了1-甲氧基,2-氯代烷烃,而对于β-取代的苯乙烯,主要的反应产物是发生苯基迁移的1,2-二甲氧基烷烃和2,2-二甲氧基烷烃。结果表明,这些反应是通过中间形成烷基苯基氯化二苯酚PhCR(OMe)CHR 1 SeCl 2 Ph来进行的,而中间反应机理取决于起始烯烃的结构。