Insertion reactions of the p-complex structure of silylenoid into C–X bonds (X = F, Cl, Br, O, and N)

The insertion reactions of the p-complex structure (A) of silylenoid H2SiLiF into C–X bonds of CH3XHn−1 (X = F, Cl, Br, O, N; n = 1, 1, 1, 2, 3) have been studied using ab initio and DFT methods. The results indicate that the insertions proceed in a concerted manner, forming H2SiXHn−1CH3 and LiF. The order of reactivity by A insertion indicates the reaction barriers increase for the same-row element X from right to left in the periodic table, whereas change very little for the same-family element X. The insertions of A and the three-membered-ring structure of H2SiLiF are similar. Both structures may participate in insertion reactions.