Ketenes are highly reactive functional groups that are commonly prepared in situ and used immediately. These molecules, of the general form R<sub>2</sub>C=C=O, possess two units of unsaturation which can react orthogonally, the C=C and C=O. The use of ketenes in organic synthesis is limited due to their propensity to dimerize and trimerize, as well as undergo nucleophilic and electrophilic attack. In compliment, silyl ketenes, those with a trialkyl silyl group on the terminal carbon, are stable due to hyperconjugation and can be prepared, isolated, and stored under common conditions. Here, we will present the use of silyl ketenes to prepare small molecules and polymers, specifically the preparation of 2-pyranones and rigid rod polymers. We will describe how both the C=C and C=O moieties of silyl ketenes undergo polymerization, yielding ketone, ester, and ketene acetal functionalities, respectively.

Silyl ketenes building blocks for complex molecules and polymers

2019 Fall National Meeting

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