ENANTIOFACE DIFFERENTIATION BY CHIRAL POLYMERS CONTAINING DIMETHYLAMINOBORNYL MOIETIES

Chiral monomers cis,endo-3-dimethylamino-2-bornyl methacrylate (DABM) and N,N-dimethyl[cis,endo-2-(2-vinyloxy-ethoxy)-3-bornyl]amine (DVEBA) were synthesized from (+)-camphor. The homopolymerization of both DABM and DVEBA, and the copolymerization of both chiral monomers with achiral methylmethacrylate (MMA) and styrene (St) were carried out with 2,2-azobisisobutyronitrile (AIBN) in various organic solvents. Effects of temperature, solvents, reagent molar ratio and reaction time on the polymerizations were studied. Dependences of the feeding concentration and reaction conditions on the specific rotation of the chiral copolymers were investigated. Enantioface differentiation by using the chiral polymers having dimethylaminobornyl moieties synthesized in this investigation were investigated. Effects of temperature and solvent on the asymmetric induction were also studied. (C) 1994 John Wiley & Sons, Inc.