Polymerization and Telomerization of Chiral Acrylamides

The acrylamide derived from Oppolzer's camphor sultam was polymerized and the resulting polymer was converted to poly (allyl acetate) through a reduction-acetylation sequence. The poly(allyl acetate) thus obtained was analyzed by NMR and was compared with authentically prepared isotactic as well as atactic poly (allyl acetate). The ¹³C NMR peaks were assigned at the tetrad level. It is concluded that the poly(allyl acetate) obtained from poly(camphor sultam acrylamide) has an isotacticity level as low as 54%. Telomerization studies indicated that this chiral auxiliary is unable to control stereochemistry for telomers with two or more monomers incorporated. A model is proposed to account for the low selectivity in these polymerizations. © 1994, American Chemical Society. All rights reserved.

Duke Scholars

Author Andrew T. McPhail Chemistry