The Radiation-Induced Addition Reaction of Ethers to Chlorofluoroolefins

Muramatsu, Hiroshige; Inukai, Kan; Ueda, Teruo

doi:10.1021/jo01031a027

Cited by 25 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The radical additions of chlorotrifluoroethylene and tetrafluoroethylene with THF were reported to yield the addition compounds even though the oligomerization of fluorovinyl compounds took place simultaneously 4) . Chambers and coworkers have also reported the radical To develop the radical polyaddition reaction of bis(a-trifluoromethyl-b-difluorovinyl) terephthalate (BFP) with 1,4-dioxane, bis(a-trifluoromethyl-b-difluorovinyl) cyclohexane-1,4-dicarboxylate (FDFC) and bis(a-trifluoromethyl-b-difluorovinyl) adipate (FDFA) were prepared and polyadditions with 1,4-dioxane, diethyl ether, and 1,2-dimethoxyethane were examined in the presence of benzoyl peroxide (BPO).…”

Section: Introductionmentioning

confidence: 99%

Novel fluorinated polymers by radical polyaddition of bis(α-trifluoromethyl-β-difluorovinyl) dicarboxylate with ether

Narita¹,

Hagiwara

Hamana

2000

Macromol. Chem. Phys.

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Novel fluorinated polymers by radical polyaddition of bis(α-trifluoromethyl-β-difluorovinyl) dicarboxylate with ether

Narita¹,

Hagiwara

Hamana

2000

Macromol. Chem. Phys.

View full text Add to dashboard Cite

show abstract

“…Muramatsu et al [11][12][13][14][15] and Liska et al 16 -18 reported the radical addition of chlorotrifluoroethylene with trialkylamines under UV or ␥-rays irradiation to afford mono-and di-addition products with relatively low yields and low selectivity, and no development to application of bifunctional fluorinated dienes with alkylamines to prepare polymers has been reported yet. The polyaddition of BFP with alkylamines was investigated.…”

Section: Polyaddition Of Bfp With Trialkylamine 35mentioning

confidence: 99%

“…[5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] No development, however, on the preparation of fluorinated polymers by radical polyaddition mechanism has been available. In this review, I recount the fluorinated polymer preparation by radical polyaddition of bisperfluoroisopropenyl compounds [CF 2 AC(CF 3 )OROC(CF 3 )ACF 2 ] with many organic counterparts possessing carbon-hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

Novel fluorinated polymers by radical polyaddition: Inspiration and progress

Narita¹

2004

J. Polym. Sci. A Polym. Chem.

View full text Add to dashboard Cite

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

show abstract

“…The high radical addition reactivity of perfluorovinyl compounds has, on the other hand, been demonstrated by many research groups [2][3][4][5][6][7][8][9][10][11][12][13][14]. Radical addition of perfluorovinyl compounds has then been developed as facile methods for preparation of fluorinated organic compounds accompanied by forming carbon-carbon bonds.…”

Section: Introductionmentioning

confidence: 99%