Kravchenko S. N-chloro-N-alkoxyamides. Reactions with nucleophilic agents

The objects is synthesis, structure and chemical properties of N-chloro-N-alkoxyamides and their derivatives. The purpose of work - development of the new methods of synthesis of amides with germinal system О-N-Х (Х=CI, OR, N+). Меthods - organic synthesis, IR- and NMR 1H spectroscopy, mass-spectrometry, X-ray and elementary analysis. Results - By structure analysis of N-Х-N-methoxyureas (X = Cl, OAc, OMe) and N,N-bis(methoxycarbonyl)-N-methoxyimide it was found that anomeric effect was predominant in N-Х-N-methoxyureas. It was found that in N-chloro-N-alkoxy-N'-arylureas the chlorine atom could be replaced by outer nucleophile and N,N-dialkoxy-N'-arylureas formed at alkoholysis in presence of silver trifluoracetate. As found the possibility of isopropanolysis of N-acyloxy-N-alkoxyureas was depended of the alkoxy group nature. Firstly N-(4-N,N-dimethyl-1-pyridinium) N-alkoxybenzamides chlorides were obtained. Area of application - organic chemistry.