Acyl iodides in organic synthesis. Reactions of acetyl iodide with urea, thiourea, and their N,N'-disubstituted derivatives

作者：Voronkov M G^*; Vlasova N N; Grigor'eva O Yu; Belousova L I; Vlasov A V

来源：Russian Journal of Organic Chemistry, 2009, 45(4): 486-490.

DOI：10.1134/S1070428009040022

Acetyl iodide reacted with urea and its derivatives to give the corresponding N-substituted products. The reactions of acetyl iodide with thiourea, N,N'-dimethylthiourea, imidazolidine-2-thione, and hexahydropyrimidine-2-thione resulted in the formation of S- or N-acetyl derivatives, depending on the temperature and structure of the sulfur functionality (thione or thiol). By contrast, in the reaction of acetyl iodide with N,N'-bis(3-triethoxysilylpropyl)thiourea one ethoxy group on the silicon atom was replaced by iodine with formation of N-{3-[(diethoxy)iodosilyl]propyl}-N'-[3-(triethoxysilyl)propyl]thiourea. The latter decomposed on heating to give 3-triethoxysilylpropyl isothiocyanate and silicon-containing polymer with the composition C(45)H(97)IN(6)O(14.5)S(3)Si(6).

• 出版日期2009-4