Polydiphenylacetylene with Schiff Base End Groups: Synthesis and Characterization

Abstract

The carbonyl–olefin exchange reaction is a new reaction between carbonyl group and olefin double bond, which has a formal similarity with the olefin metathesis – one carbon atom in the latter is replaced with an oxygen atom. Till now the new reaction is performed successfully only when the two functional groups (carbonyl group and olefin double bond) are in one molecule and are conjugated. The α, β-unsaturated carbonyl compounds (substituted propenones) are the compounds with such a structure. They polymerize giving substituted polyacetylenes. The chain propagation step of this polymerization is in fact the carbonyl–olefin exchange reaction. The question arises: is it possible the carbonyl–olefin exchange reaction to take place when the two functional groups are not in one molecule and are not conjugated, and could this reaction become an alternative of the existing carbonyl olefination reactions?