Cumulated double bonds are curious functional groups of two double bonds sharing a central carbon in which the pi systems are not conjugated; examples include ketenes (C=C=O), allenes (C=C=C), and the more ubiquitous isocyanates (N=C=O). Of these, ketenes in which the terminal carbon bears hydrogen, alkyl, or aryl groups, are highly reactive moieties that are commonly prepared in situ and used immediately without isolation due to their propensity to undergo dimerization and trimerization reactions. In contrast, silyl ketenes, in which the terminal carbon contains a trialkyl(aryl) silyl group are isolable due to stability provided by hyperconjugation (e.g., the beta silicon effect). This presentation will address our efforts to polymerization silyl ketenes and control regioreactivity to give polyketone, polyketene acetal, and polyesters. Secondary reactions, including the production of highly functionalized small molecules will be discussed.

Silly reactions of silyl ketenes

ACS Spring Meeting 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.