Polymerization of Unsaturated Sugars II. Radical Copolymerization of a Furanoid Glucal, 3-O-Benzyl-1,2-dideoxy-5,6-O-isopropylidene-d-arabino-hex-1-enofuranose

TLDR: A stable furanoid glucal, 3-O-benzyl-1,2-dideoxy-5,6-Oisopropylidene-d-arabino-hex-1-enofuranose (BIF) was synthesized, and the equilibrium association constant K for the charge-transfer complex formation with maleic anhydride in CDCl3 at 25°C was 0.131 mol−1 as determined by 13C NMR as discussed by the authors.

Abstract: A stable furanoid glucal, 3-O-benzyl-1,2-dideoxy-5,6-O-isopropylidene-d-arabino-hex-1-enofuranose (BIF) was synthesized, and the equilibrium association constant K for the charge-transfer complex formation with maleic anhydride in CDCl3 at 25°C was 0.131 mol−1 as determined by 13C NMR. BIF copolymerized with maleic anhydride almost alternatingly, AIBN being used as the initiator. Other electron accepting monomers such as N-phenylmaleimide and acrylonitrile also copolymerized with BIF. Terpolymerization of BIF-maleic anhydride-acrylonitrile gave the copolymer containing BIF residues.