Reactions of thioamides with metal carboxylates in organic solvents ar
e described. These processes enable the selective preparation of nitri
les, imides or amides depending on the substitution pattern of the sta
rting material. Mechanistic hypotheses supported by experimental evide
nces, including the unequivocal synthesis of bis(thioacetanilide)mercu
ry(II) as a key reaction intermediate, are also proposed. (C) 1997 Els
evier Science Ltd.