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Novel Spontaneous Polymer Formation from Acetaldehyde Azine and Maleic Anhydride via Radical Mechanism

2000; American Chemical Society; Volume: 33; Issue: 17 Linguagem: Inglês

10.1021/ma000183+

1520-5835

Akihito Hashidzume, Tetsuya Noda, Yotaro Morishima, Atsushi Kajiwara, Mikiharu Kamachi,

Supramolecular Chemistry and Complexes

A THF-insoluble polymeric product was obtained by the reaction between acetaldehyde azine (AcAz) and maleic anhydride (MAnh) without any initiator. The reduced viscosity values for this product indicate polymer formation from AcAz and MAnh. Results of the reactions between AcAz and MAnh at varying feed ratios of AcAz indicate that the polymer is formed mainly by reaction between equimolar amounts of AcAz and MAnh. (2Z)-4-{1-(5-Methyl-2-pyrazolinyl)}-4-oxo-2-butenoic acid (compound 1), a one-to-one adduct of AcAz with MAnh, was isolated as a crystalline compound from the THF-soluble fraction of the reaction mixture. Comparing the spectroscopic results for the polymer with those for compound 1 and 4-{1-(5-methyl-2-pyrazolinyl)}-4-oxobutanoic acid (compound 2), a one-to-one adduct of AcAz with SAnh, the polymer from AcAz and MAnh was found to be formed mainly by polymerization of compound 1 through the CC bond. Results of the polymerizations of compound 1 using typical initiators show compound 1 can be polym...