Mechanism of chlorotriflamidation of vinylsilanes with N,N-dichlorotriflamide

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Abstract

The mechanism of the reaction of vinylsilanes with N , N -dichlorotriflamide and the effect of a substituent at the silicon atom on the reaction course and on the charge distribution in substrates and their carbon analogues were studied by DFT method. The C=C bond in vinylsilanes and alkenes is polarized in the opposite way. The reaction proceeds in two stages: chlorination of the substrate with the formation of a chloronium ion, and its opening at the Cβ-Cl bond by the N -chlorotriflamide anion. Transition states of two stages were calculated. The reaction products are hydrolyzed to NH-derivatives; their IR spectra and supramolecular structure, including cyclic and linear dimers, calculated in the gas phase and in a polar medium, were studied.

About the authors

N. N Chipanina

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

L. P Oznobikhina

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

I. V Ushakova

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

B. A Shainyan

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: bagrat@irioch.irk.ru

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