Radical polyaddition reaction of bis(α-trifluoromethyl-β,β-difluorovinyl) 2,3,5,6-tetrafluoroterephthalate

Fujiwara, Hirotada; Narita, Tadashi; Hamana, Hiroshi; Kurata, Ryo

doi:10.1016/j.jfluchem.2003.10.003

Journal of Fluorine Chemistry

2004

DOI: 10.1016/j.jfluchem.2003.10.003

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Radical polyaddition reaction of bis(α-trifluoromethyl-β,β-difluorovinyl) 2,3,5,6-tetrafluoroterephthalate

Hirotada Fujiwara¹,

Tadashi Narita²,

Hiroshi Hamana³

et al.

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Novel fluorinated polymers by radical polyaddition: Inspiration and progress

Narita¹

2004

J. Polym. Sci. A Polym. Chem.

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The story of the outset and the growth of radical polyaddition of bisperfluoroisopropenyl derivatives [CF2C(CF3)R C(CF3) CF2] with several organic compounds possessing carbon–hydrogen bonds is described. The reaction afforded novel fluorinated polymers bearing such organic segments in polymer main chains as 1,4‐dioxane, diethyl ether, dimethoxyethane, 18‐crown‐6, triethylamine, glutaraldehyde, and alkanes which have never been supposed as direct starting compounds for preparation of polymers. The facile method for preparation of fluorinated hybrid polymers bearing alkylsilyl groups was developed with diethoxydimethylsilane and silsesquioxanes. Taking advantage of the high reactivity of the perfluoroisopropenyl group as a radical acceptor, self‐polyaddition and cyclopolymerization were investigated. Triethysilyl perfluoroisopropenyl ether [CF2 C(CF3)OSi(C2H5)3] was proved to be the most probable candidate for self‐polyaddition. Cyclopolymerization of perfluoroisopropenyl vinylacetate [CF2C(CF3) OCO CH2CH CH2] was investigated to afford polymers possessing five‐membered‐ring units in main chains. The interconversion of the unstable fluorinated carbon radical and the stable hydrocarbon radical had an important role in the reaction. The radical addition reaction presented herein may be developed for preparation of a wide variety of novel fluorinated polymers and organic compounds possessing functional groups. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 4101–4125, 2004

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Novel fluorinated polymers by radical polyaddition: Inspiration and progress

Narita¹

2004

J. Polym. Sci. A Polym. Chem.

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Radical polyaddition reaction of bis(α-trifluoromethyl-β,β-difluorovinyl) 2,3,5,6-tetrafluoroterephthalate

Cited by 1 publication

References 10 publications

Novel fluorinated polymers by radical polyaddition: Inspiration and progress

Novel fluorinated polymers by radical polyaddition: Inspiration and progress

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