Synthesis of Furan-Based Poly(Ethylene Glycol) Derivatives and Their Diels-Alder Reactions
Date of Graduation
Master of Science in Chemistry
Poly (ethylene glycol) (PEG) and its derivatives exhibit many useful properties, which have led to a vast array of biomedical and biotechnical applications. Several PEG derivatives have been prepared for use in these applications. However, there is a continuous interest in new PEG derivatives that are easily prepared and possess useful properties. In this work, we have synthesized two new furan-based PEG derivatives namely, 2-[methoxypoly(oxyethylene) furan and 3-[methoxypoly(oxyethylene)methylene]furan. The Diels-Alder reactions of the above derivatives with maleic anhydride, N-phenylmaleimide, N-2-mehylphenylmaleimide, maleimide, and diethylacetylene dicarboxylate have been investigated. The products of these reactions have been characterized by spectroscopic techniques such as ¹H NMR, ¹³C NMR and IR. In addition, aromatization of the Diels-Alder adducts obtained from the reaction of 5-[methoxypoly(oxyethylene)]-(3E)-1, 3 pentadiene amd 5-methoxyethoxy-(3E)-1, 3-pentadiene with diethylacetylene dicarboxylate by DDQ has been achieved, and these products have also been characterized by spectroscopic techniques.
© Almary Chacon
Chacon, Almary, "Synthesis of Furan-Based Poly(Ethylene Glycol) Derivatives and Their Diels-Alder Reactions" (2001). MSU Graduate Theses. 2400.