Synthesis of 1-Methoxypoly(oxyethylene)benzocyclobutene and Its Diels-Alder Reactions

Abstract

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.

Department(s)

Chemistry and Biochemistry

Document Type

Article

DOI

https://doi.org/10.1002/pola.20037

Keywords

Benzocyclobutene, Biocompatibility, Biological applications of polymers, Biopolymers, Diels-alder reaction, Drug delivery systems, Maleic anhydride, N-phenylmaleimide, O-toluidine, Poly(ethylene glycol), Poly(oxyethylene)

Publication Date

4-15-2004

Journal Title

Journal of Polymer Science, Part A: Polymer Chemistry

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