Synthesis of 1-Methoxypoly(oxyethylene)benzocyclobutene and Its Diels-Alder Reactions
A new poly(ethylene glycol) derivative, 1-methoxypoly(oxyethylene) benzocyclobutene (1) was prepared from the reaction of 1-benzocyclobutenyl 1-hydroxyethyl ether with mesylate of methoxypoly(oxyethylene) in tetrahydrofuran. The degree of end-group conversion, as determined by NMR, was 100%. The Diels-Alder reactions of 1 with maleic anhydride and N-phenylmaleimide were carried out in refluxing toluene to obtain the corresponding adducts (2 and 3, respectively) in excellent yields. NMR analyses of 2 and 3 indicated complete conversion of 1 to the corresponding products. The reaction of 2 with o-toluidine resulted in complete conversion of the anhydride adduct to the corresponding products.
Benzocyclobutene, Biocompatibility, Biological applications of polymers, Biopolymers, Diels-alder reaction, Drug delivery systems, Maleic anhydride, N-phenylmaleimide, O-toluidine, Poly(ethylene glycol), Poly(oxyethylene)
Herati, Reza Sedaghat, and Ramin Sedaghat Herati. "Synthesis of 1‐methoxypoly (oxyethylene) benzocyclobutene and its diels–alder reactions." Journal of Polymer Science Part A: Polymer Chemistry 42, no. 8 (2004): 1934-1938.
Journal of Polymer Science, Part A: Polymer Chemistry