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Alexander B. Rozhenko, Sergiy S. Mykhaylychenko, Nadiya V. Pikun, Yuriy G. Shermolovich and Jerzy Leszczynski Intermediate carbene formation in the reaction of thioamides with phosphorus (III) derivatives: Quantum chemical investigation International Journal of Quantum Chemistry 114

Version of Record online: 8 OCT 2013 | DOI: 10.1002/qua.24546

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Theoretical methods are valuable for the study of highly reactive intermediaries in reactions. This work studies the mechanism of the recently reported reaction of (perfluoro)alkyl (thio)amides with phosphorus(III) derivatives. The formation of short-lived perfluoroalkyl carbenes is predicted as a probable intermediate in the reaction of perfluoroalkyl thioamides with trimethyl phosphites and tris(dimethylamino)phosphine. Adding the second mole of the phosphorus(III) derivative to the carbene is thermodynamically favored. The formed phosphorus ylides undergo further transformations.

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