Nef-isocyanide–Perkow synthesis of new polarized olefins containing 2-dicyanomethylene-2,3-dihydrothiazole and 2-dicyanomethylene-1,3-dithiole moieties

Imidoyl chlorides (generated from isocyanides and acyl chlorides) reacts with triisopropyl phosphite, in a Perkow-type reaction, to produce 1-alkoxycarbonyl-2-(alkylimino)vinyl diisopropyl phosphate, which undergo a smooth reaction with bidentate nucleophilic intermediates obtained from the reaction between malononitrile and heterocumulenes, such as arylisothiocyanates or carbon disulfide to produce polarized olefins containing 2-dicyanomethylene-2,3-dihydrothiazole and 2-dicyanomethylene-1,3-dithiole moieties.