Synthesis of terpolymers by spontaneous copolymerization of the cyclobutane adducts of electron-acceptor olefins and vinyl ether with 2-oxazolines

• Published in: Tetrahedron Vol. 53; no. 45; pp. 15603 - 15616
• Main Authors: Yokozawa, Tsutomu, Tagami, Masato, Takehana, Tomoyuki, Suzuki, Tadashi
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 10-11-1997
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(97)00981-2

Spontaneous copolymerizations of the cyclobutane adducts of strong donor olefins and strong acceptor olefins, 1,1,2,2-tetracyano-3-ethoxycyclobutane (
1a) and dimethyl 2,2-dicyano-3-ethoxycyclobutane-1,1-dicarboxylate (
1b), with 2-oxazolines (
2) are described. In the reaction of
1b with 2-methyloxazoline (
2b), the alternating copolymer of
1b and
2b, the 1:1:1 periodic terpolymer of dimethyl 1,1-dicyanoethylene-2,2-dicarboxylate, vinyl ether, and
2b, was obtained. Cyclobutane
1a also reacted with
2b to yield copolymer rich in
1a
The titled compounds undergo spontaneous copolymerization to yield the alternating copolymer, the 1:1:1 terpolymer of the two olefins and 2-oxazoline.