Syntheses and radical polymerizations of novel optically active vinyl and isopropenyl carbamates having L-leucine structures

✍ Scribed by Fumio Sanda; Toru Abe; Takeshi Endo

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 500 KB
• Volume: 34
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19960730)34:10<1969::aid-pola15>3.0.co;2-g

✦ Synopsis

Syntheses and radical polymerizations of vinyl and isopropenyl carbamates having L-leucine methyl ester structures, N-vinyloxycarbonyl-L-leucine methyl ester (VOC-L-M) and Nisopropenyloxycarbonyl-L-leucine methyl ester (IOC-L-M), were carried out. VOC-L-M and IOC-L-M were prepared by the reactions of L-leucine methyl ester with vinyl and isopropenyl chloroformates in the presence of sodium hydrogen carbonate. The radical polymerization of VOC-L-M with AIBN (1 mol %) in bulk, chlorobenzene, methanol, and N,N-dimethylformamide afforded the corresponding polymer (poly(V0C-L-M)) with M,, 7,400-19,000. Meanwhile, IOC-L-M afforded no polymer with AIBN a t 60°C but afforded a polymer having low molecular weight with BPO at 80°C. The glass transition temperatures of poly(V0C-L-M) and poly(I0C-L-M) were 53 and 65"C, respectively. The 10% weight loss temperatures of poly(V0C-L-M) and poly(I0C-L-M) under nitrogen were 255 and 173, respectively. The copolymerization parameters of VOC-L-M (M,) and vinyl acetate ( M 2 ) were evaluated as r, = 0.92 and r, = 0.63.