Pedro Ramiro

On the mechanism of reaction between ketones and nitriles. Unexpected results from benzyl nitriles

Abstract Benzyl nitriles bearing electron donating groups react with ketones in the presence of trifluoromethanesulfonic anhydride to form naphthalene amines and related compounds. In contrast, the same benzyl nitriles substituted with electron withdrawing groups form the corresponding 2,4-dibenzyl substituted pyrimidines. A mechanism is proposed that explains the divergence in reaction paths leading to these products.

The reaction of thioesters with nitriles. A new synthetic approach to the preparation of substituted 4-alkylthio- and 4-arylthiopyrimidine derivatives

Abstract S -Alkyl and S -aryl thioesters react with nitriles in the presence of triflic anhydride to form substituted 4-alkylthio- and 4-arylthiopyrimidines. However, when methyl thiocyanate is used as nitrile, dithioimidocarbonates are formed. A mechanism to explain these differences is postulated.