Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β-chloroacrylamides
作者:Maureen Murphy、Denis Lynch、Marcel Schaeffer、Marie Kissane、Jay Chopra、Elisabeth O'Brien、Alan Ford、George Ferguson、Anita R. Maguire
DOI:10.1039/b618540a
日期:——
Treatment of a series of alpha-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous alpha-thio-beta-chloroacrylamides. The mechanistic pathway has been established through isolation and characterisation of intermediate compounds. The scope of the transformation has been explored-aryl and alkylthio substituents, primary, secondary and tertiary amides can be employed
用N-氯代琥珀酰亚胺处理一系列的α-硫代酰胺可有效地转化为类似的α-硫代-β-氯丙烯酰胺。通过分离和表征中间化合物已经建立了机理途径。已经探讨了转化的范围-芳基和烷硫基取代基,可以使用伯,仲和叔酰胺。在大多数情况下,氯丙烯酰胺仅作为Z-立体异构体形成。但是,用叔丙酰胺或衍生自丁酸或戊酸的酰胺会形成E-和Z-立体异构体的混合物。