Detection of some formiminoesters and the measurement of their rates of formation using NMR

Autor: Nematollahi, Jay, Tuck, L.Dallas
Zdroj: Journal of Pharmaceutical Sciences; June 1967, Vol. 56 Issue: 6 p684-687, 4p
Abstrakt: Formiminoesters have long been postulated as intermediates in the synthesis of formamidines and various heterocyclic compounds. The methyl, ethyl, and isopro-pyl homologs have been prepared by interaction of hydrogen cyanide with the appropriate alcohol in the presence of dry hydrogen chloride, and the progress of the formation was monitored by NMR at regulated probe temperatures from —25° to 0°. The rate of formation of formiminoesters depends principally on the concentration of hydrogen cyanide. The quartet in the NMR spectrum at a chemical shift near 8 p.p.m. arises from a single proton on a doubly bonded carbon, which is coupled to two nonequivalent protons. This is consistent with the structure:The lifetime of the nitrogen-proton bond is of the order of 3sec.
Databáze: Supplemental Index