Synthesis and Polymerisation Behaviour of 2-Aryl-5-methylene-1,3-dioxolan-4-ones and Arylbis(5-methylene-1,3-dioxolan-2-yl-4-on)es

Article abstract of DOI:10.1002/prac.199533701102

Starting from 2,6-di(hydroxymethyl)-4-methylphenol-Na-salt-1-hydrate (1) a synthesis of 2-alkoxy-5-methylisophthaldialdehydes (3a,b) is described via alkylation and oxidation.Condensation of aromatic aldehydes with 3-bromo-2-hydroxypropanoic acid (β-bromolactic acid) affords diastereoisomeric mixtures of new 2-aryl-5-bromomethyl-1,3-dioxolan-4-ones (6a-h) as well as the corresponding bisdioxolanones (6i-l).Dehydrobromination of 2-aryl-5-bromomethyl-1,3-dioxolan-4-ones (6a-d,i) with DBU leads to 2-aryl-5-methylene-1,3-dioxolan-4-ones (8a-e).Polymerization of compounds 8a,b,d and e proceed via opening of the dioxolanone ring.