Reactions of N-alkyl- and N-aryltrihalogenoacetamides with phosphorus pentachloride |
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Authors: | A. D. Sinitsa A. A. Shalimov A. M. Nesterenko D. M. Malenko |
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Affiliation: | (1) Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, 5 ul. Murmanskaya, 02660 Kiev 94, Ukraine |
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Abstract: | In the study of reactions of N-alkyl- and N-aryltrihalogenoacetamides with PCl5, it was demonstrated for the first time that 3-alkyl(aryl)-2,2,2,4 tetrachloro-4-trihalomethyl-1,3,2-λ5-oxazaphosphetanes are intermediates in the synthesis of trihaloacetimidoyl chlorides. According to quantum-chemical calculations, acyclic N-tetrachlorophosphoranes, which are the primary products in the reactions of trihaloacetamides with PCl5, undergo rapid cyclization into the corresponding phosphorates and subsequent 1,3-chlorotropic migration gives rise to oxazaphosphetanes with the five-coordinate P atom.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 739-744, March, 2005. |
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Keywords: | trihaloacetamides phosphorus pentachloride tetrachlorophosphoranes imidoyl chlorides oxazaphosphetanes quantum chemical calculations |
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