Thioiminium and thiaphospholanium derived from acetonitrile via nickel(ii)–(2-mercaptophenyl)phosphine complexation

Abstract

[Ni(P(o-C₆H₄S)(o-C₆H₄SC(CH₃)NH₂)(C₆H₅))₂](ClO₄)₂ (2) with two thioiminium functionalities is derived from CH₃CN solvent under anhydrous conditions. Moreover, thiaphospholanium salts, [(C₆H₅)P(C₆H₄SC(CH₃)(NHCOCH₃))(o-C₆H₄SH)](ClO₄) (3) and [(C₆H₅)₂-P(C₆H₄SC(CH₃)(NH₃))](ClO₄)₂ (5), can be obtained through a similar Pinner-type nitrile activation. These results demonstrate the possible intermediate of enzymatic nitrile transformation and also provide an approach to the preparation of 2-amino-1,3-benzothiaphospholanium derivatives.