1978 Volume 51 Issue 12 Pages 3544-3548
Nonenzymatic dihydronicotinamide reduction of carbon-carbon double bonds occurs with the aid of Mg2+ ion or acetic acid. The role of Mg2+ ion and acetic acid is discussed on the basis of spectral studies, kinetic measurements, and product analyses. The addition of Mg2+ ion caused the shift of the NMR peak of substrate α-proton to lower field, and the magnitude was parallel to the yield of reduced methylene derivatives. Kinetic studies suggested that the dihydronicotinamide reduction in the presence of Mg2+ ion is most reasonably understood by assuming a competitive complexation of dihydronicotinamide and substrate with Mg2+ ion. On the other hand, acetic acid aids the reduction by means of general acid catalysis, but an alternative mechanism is suggested for the reduction of benzylidenemalononitrile.
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