Mechanism of chlorotriflamidation of vinylsilanes with <i>N</i>,<i>N</i>-dichlorotriflamide

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.