Pyridinium salts and dihydropyridines; mechanistic studies of the redox reaction between pyridinium salts and alkoxides in tetrahydrofuran

A model system for NAD-dependent redox reactions has been designed in an attempt to assess the involvement of covalent adducts as intermediates. The system consists of 3-substituted 1-n-heptylpyridinium salts and substituted benzyl alkoxides. Although covalent adducts were found in the reaction mixture, studies of substituent effects and other structural variations did not show that a covalent intermediate is on the reaction path.