Polymerization and Telomerization of Chiral Acrylamides

Article abstract of DOI:10.1021/jo00085a017

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 54percent.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.