SYNTHESIS AND POLYMERIZATION BEHAVIOR OF 2-ARYL-5-METHYLENE-1,3-DIOXOLAN-4-ONES AND ARYLBIS(5-METHYLENE-1,3-DIOXOLAN-2-YL-4-ON)ES

Starting from di(hydroxymethyl)-4-methylphenol-Na-salt-1-hydrate (1) a synthesis of 2-alkoxy-5-methylisophthaldialdehydes (3a,b) is describe d via alkylation and oxidation. Condensation of aromatic aldehydes wit h 3-bromo-2-hydroxypropanoic acid (beta-bromolactic acid) affords dias tereoisomeric mixtures of new 2-aryl-5-bromomethyl-1,3-dioxolan-3-ones (6a-h) as well as the corresponding bisdioxolanones (6i-l). Dehydrobr omination of 2-aryl-5-bromomethyl-1,3-dioxolan-4-ones (6a-d,i) with DB U leads to 2-aryl-5-methylene-1,3-dioxolan-4-ones (8a-e). Polymerizati on of compounds 8a,b,d and e proceed via opening of the dioxolanone ri ng.