Poly(silyl ketene)s are a proposed class of polymers with potential for a range of desirable properties, such as degradability. Since ketenes can undergo a variety of reactions, such as propagation via the C=C and C=O moieties, it is important to establish the fundamental reactivities of silyl ketene monomers so that products can be predicted and reactions can be planned. This work presents computational studies of the activation of silyl ketene monomers by reaction with nucleophiles. Depending on the nature of the nucleophile and monomer, activation occurs via nucleophilic addition to, respectively, deprotonation of the monomer. Systematic studies of reactivities were performed to characterize the kinetics and thermodynamics of deprotonation versus nucleophilic addition and systematic trends were investigated in order to rationalize and gain greater control over silyl ketene reactivity.

Computational studies of nucleophilic addition versus deprotonation in silyl ketenes

ACS Spring 2022

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