USE OF READILY AVAILABLE MONOMERS IN THE SYNTHESIS OF VINYL COPOLYMERS WITH OPTICAL-ACTIVITY ARISING FROM THE CONFIGURATION OF STEREOGENIC CARBON-ATOMS IN THE MAIN-CHAIN

The present work was aimed at synthesising vinyl copolymers with optic al activity arising only from the configuration of the stereogenic car bon atoms in the main chain. By copolymerising optically active dieste rs of fumaric acid with styrene, backbones with a composition of simil ar to 2:1 (styrene:fumarate) were obtained displaying strongly negativ e optical rotations. Cleavage of the optically active alcohol auxiliar ies from the side chain yielded corresponding styrene-fumaric acid cop olymers displaying a small positive optical rotation. Thus, propagatio n occurs in these copolymerisations with asymmetric induction to gener ate a main chain with its own intrinsic asymmetry and corresponding op tical activity. The mechanism of the induction is discussed. Correspon ding copolymers involving isobutyl vinyl ether (IBVE) or dec-1-ene wer e synthetically more problematical and this is also discussed.