Oxa‐ and Thiazolidine‐Containing Polymers Derived via the Asinger Four‐Component Reaction: the Ring Matters. Issue 5 (24th January 2014) - Sehlinger, Ansgar
Abstract Novel structural motifs in macromolecular chemistry are introduced by the use of the Asinger multicomponent reaction. The combination of ammonia, acetone, α‐chloroisobutyraldehyde, and either water or sodium hydrosulfide, leads to an oxazoline or thiazoline scaffold, respectively, which is subsequently modified with 10‐undecenol and 10‐undecenoyl chloride to obtain heterocycle‐functionalized α, ω‐dienes. These substrates are used as monomers in an acylic diene metathesis (ADMET) or thiol‐ene step‐growth polymerization. The thus‐obtained polymers are studied in post‐polymerization modifications, like hydrogenation and oxidation. Here, the thiazolidine‐ and oxazolidine‐containing polymers show dramatically different chemical stability due to the heterocyclic moieties.