Abstract
In order to know the influence of the substitute at the 3-position in the reduction of pyridinium salt by NaBH4, the reduction of 1-methyl-3-cyanopyridinium iodide and 1, 3-dimethylpyridinium iodide by NaBH4 was carried out. It was found that the former gave quite a similar type of reductive product to that of 3-methoxycarbonyl derivative but the latter gave a different type of reductive product. This difference might be considered that the cyano group possess the same electro-philic property to the methoxycarbonyl group but the methyl group might possess electron-donor properties. Therefore, the influence of the substitute in the reaction may be controlled by rather electronic behavior than steric configuration.
