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Polymerization of meta-naphthoquinone methide: 3,4-benzo-6-methylenebicyclo [3.1.0] hex-3-ene-2-one

✍ Scribed by Takahito Itoh; Yasusi Matsumura; Masataka Kubo

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 160 KB
Volume: 35
Category: Article
ISSN: 0887-624X
DOI: 10.1002/(sici)1099-0518(199703)35:4<741::aid-pola19>3.0.co;2-n

No coin nor oath required. For personal study only.

✦ Synopsis

Polymerization behavior of meta-naphthoquinone methide, 3,4-benzo-6methylenebicyclo[3.1.0]hex-3-ene-2-one ( 1), was studied. Radical initiator 2,2-azobis(isobutyronitrile) (AIBN) induced polymerization of 1, but ionic initiators potassium tert-butoxide, butyllithium, and boron trifluoride etherate did not. Polymerization of 1 proceeded via ring-opening and aromatization to give a polymer with head-to-tail monomer unit placement. Compound 1 copolymerized with methyl methacrylate (MMA) in the presence of AIBN to obtain the monomer reactivity ratios r 1 (1) Å 0.28 { 0.07 and r 2 (MMA) Å 0.39 { 0.02 at 60ЊC and Q and e values of Q Å 1.04 and e Å 01.03, indicating that 1 is a conjugative and electron-donating monomer. Ring-opening and aromatization of 1 also took place in the copolymerization.

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