Syntheses and radical polymerization behavior of novel optically active methacrylamides having (L)-leucine structure in the side chains

✍ Scribed by Fumio Sanda; Masafumi Nakamura; Takeshi Endo

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 240 KB
• Volume: 36
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19981115)36:15<2681::aid-pola2>3.0.co;2-3

✦ Synopsis

Syntheses and radical polymerizations of methacrylamides having (L)leucine and N-methyl-(L)-leucine methyl ester structures in the side chains N-methacryloyl-(L)-leucine methyl ester (MA-L-M) and N-methyl-N-methacryloyl-(L)-leucine methyl ester (N-Me-MA-L-M) were carried out. The monomers were prepared by the reactions of methacryloyl chloride with the corresponding amino acid methyl esters. Radical polymerizations were carried out in the presence of appropriate initiators at 60°C and 120°C. MA-L-M afforded the corresponding polymer with M n s 38,000 ϳ 372,000 in high yields, while N-Me-MA-L-M afforded a trace amount of polymer at 60°C and in a low yield even at 120°C. Both inversion and increase of absolute value of specific rotation were observed in the transformation from MA-L-M (ϩ1.3°C) to poly(MA-L