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Marchenko A.P.,Institute of Organic Chemistry Kyiv 02094 Ukraine | Koidan G.N.,Institute of Organic Chemistry Kyiv 02094 Ukraine | Hurieva A.N.,Institute of Organic Chemistry Kyiv 02094 Ukraine | Rozhenko A.B.,Institute of Organic Chemistry Kyiv 02094 Ukraine | Kostyuk A.N.,Institute of Organic Chemistry Kyiv 02094 Ukraine
Heteroatom Chemistry | Year: 2015

Cyclic zwitterionic phosphoranides 2a,b were found to be intermediate products in the reaction of N,N-dimethyl-N′-(aryl)formamidines with PBr3. The structure of phosphoranide 2a was determined by means of the X-ray and quantum chemistry investigations. Mechanism of its formation was proposed based on Density functional theory (DFT) calculations. Reactions of 2 with amines and selenium yielded either C-phosphorylated formamidines or benzazaphospholes. The first example of intramolecular heterocyclization of a pentavalent phosphorus derivative 15b into 3N{cyrillic}-1,3-benzazaphosphole has been demonstrated. © 2015 Wiley Periodicals, Inc.

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