Addition of Nitriles to Two Brook Silenes

Abstract

The addition of acetonitrile and propionitrile to two Brook silenes, (Me3Si)2SiC(OSiMe3)R where R = 1-Ad and t-Bu, was examined. Products derived from addition of the α-CH of the nitrile across the silicon–carbon double bond were identified. The reactivity of Brook silenes and naturally polarized silenes toward nitriles is compared.

Electronic effects of substituents on the reactivity of silenes: a computational analysis

“…By nature, silenes are highly reactive, and their typical reactions are [1 -2] addition to C -Si bond with variety of reactants and [2+2] cycloaddition with reagents such as carbonyl compounds and alkenes possessing multiple bonds [17][18][19][20][21][22][23]. In the absence of such reagents, their reactive nature tempts them to undergo self-cyclisation, culminating in the formation of cyclic dimers, usually by head-to-tail [2 + 2] cycloaddition mechanism.…”