Theoretical insights into the reaction between vinylidenesilanediyl and double bond compounds (formaldehyde and methyleneimine): the formation of heterocyclic silylene and spiro-Si-heterocyclic compounds

Abstract

The reaction mechanism between vinylidenesilanediyl and doubly bonded compounds (formaldehyde and methyleneimine) has been systematically investigated employing the second-order Møller-Plesset perturbation theory (MP2) method in order to better understand the reactivity of vinylidenesilanediyl. Geometry optimizations and vibrational analyses have been performed for the stationary points on the potential energy surfaces of the system. Calculations show that the four-membered heterocyclic silylene intermediate and Si-heterocyclic conjugated diene compound could be produced through addition and rearrangement processes between vinylidenesilanediyl and double bond compound. The silylene intermediate can react with second formaldehyde (or methyleneimine) to form a spiro-Si-heterocyclic product. The present study is helpful to understand further characterization of the C2H2Si molecular system and to offer an alternative approach to the formation of heterocyclic silylene and spiro-Si-heterocyclic compounds.