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Syntheses and radical polymerizations of optically active (meth)acrylamides having amino acid moieties

✍ Scribed by Fumio Sanda; Toru Abe; Takeshi Endo

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 183 KB
Volume: 35
Category: Article
ISSN: 0887-624X
DOI: 10.1002/(sici)1099-0518(19970930)35:13<2619::aid-pola9>3.0.co;2-l

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✦ Synopsis

Syntheses and radical polymerizations of several (meth)acrylamides having L-amino acid moieties were examined. The monomers were prepared by the reactions of L-amino acid ester hydrochlorides with (meth)acryloyl chloride in the presence of triethylamine in satisfactory yields. Radical polymerizations of the monomers were carried out in the presence of AIBN (1 mol %) in bulk and in several solvents to afford the corresponding polymers in satisfactory yield. The glass transition temperatures and specific rotations of the polymers depended on the substituents of the L-amino acid moieties. Nearly the same specific rotations were observed for the monomers and the model compounds of the polymer units, N-pivaloyl amino acid methyl esters. On the contrary, the specific rotations of the polymers shifted to the negative direction in ca. 30Њ. The interaction between the polymer side chains might affect the changes in the specific rotations from monomers to polymers.

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