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Synthesis and radical polymerization of an optically active monomer derived from cysteine

机译:Synthesis and radical polymerization of an optically active monomer derived from cysteine

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摘要

The synthesis and radical polymerization of N-methacryloyl-S-trityl-L-cysteine methyl ester MA-C(Trt)-M were examined. The radical polymerization was carried out at 60deg C for 20 h in the presence of 2,2'-azoisobutyronitrile (AIBN) in benzene, PhCl, and N,N-dimethylformamide (DMF) to afford the corresponding polymer with M-bar_n's in the range of 13 200-130 000 in good yields. In the radical copolymerizations of MA-C(Trt)-M with methyl methacrylate and trityl methacrylate, the specific rotations of the copolymers showed maximum values with MA-C(Trt)-M contents of 60 and 80 mol-, respectively. The polymers were treated with HBr/CH_3CO_2H (30 wt.-) to afford the trityl group-free polymers, which were insoluble in solvents due to the oxidative crosslinking reaction between the thiol groups.

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