Self-polyaddition of triethylsilyl perfluoroisopropenyl ether

Hirotada Fujiwara; Tadashi Narita; Hiroshi Hamana

doi:10.1002/pola.10819

Self-polyaddition of triethylsilyl perfluoroisopropenyl ether

Hirotada Fujiwara, Tadashi Narita, Hiroshi Hamana

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

The results on radical self-polyaddition reactivity of two trialkylsilyl perfluoroisopropenyl ethers, triethysilyl perfluoroisopropenyl ether [CF₂=C(CF₃)OSi(C₂H₅)₃] (FTEE) and dimethylphenylsilyl perfluoroisopropenyl ether [CF₂=C(CF₃)OSi(CH₃)₂C₆ H₅] (DMPE), and two perfluoroisopropenyl carboxylates, 2-butyroxypentafluoropropene [CF₂=C(CF₃)OCOC₃H₇] (BuFPP) and 2-(methoxyacetoxy)pentafluoropropene [CF₂=C(CF₃)OCOCH₂OCH₃] (MFPP), are described. Radical self-polyaddition of FTEE afforded a polymer as high as 1.87 × 10⁴ in molecular weight in the presence of radical generators such as benzoyl peroxide and di-tert-butyl peroxide. DMPE gave only addition products with initiating radicals. BuFPP and MFPP scarcely yielded even addition products with radical. The mechanism that the self-polyaddition of FTEE was initiated by the addition of radical onto the perfluoroisopropenyl group followed by a 1,5-shift to afford a methyl radical that attacked the perfluoroisopropenyl group of another FTEE molecule is proposed.

Original language	English
Pages (from-to)	2743-2754
Number of pages	12
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	41
Issue number	18
DOIs	https://doi.org/10.1002/pola.10819
Publication status	Published - Sept 15 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Polymers and Plastics
Organic Chemistry
Materials Chemistry

Access to Document

10.1002/pola.10819

Cite this

@article{3b97972935b34cbaae152c8e647479b6,

title = "Self-polyaddition of triethylsilyl perfluoroisopropenyl ether",

abstract = "The results on radical self-polyaddition reactivity of two trialkylsilyl perfluoroisopropenyl ethers, triethysilyl perfluoroisopropenyl ether [CF2=C(CF3)OSi(C2H5)3] (FTEE) and dimethylphenylsilyl perfluoroisopropenyl ether [CF2=C(CF3)OSi(CH3)2C6 H5] (DMPE), and two perfluoroisopropenyl carboxylates, 2-butyroxypentafluoropropene [CF2=C(CF3)OCOC3H7] (BuFPP) and 2-(methoxyacetoxy)pentafluoropropene [CF2=C(CF3)OCOCH2OCH3] (MFPP), are described. Radical self-polyaddition of FTEE afforded a polymer as high as 1.87 × 104 in molecular weight in the presence of radical generators such as benzoyl peroxide and di-tert-butyl peroxide. DMPE gave only addition products with initiating radicals. BuFPP and MFPP scarcely yielded even addition products with radical. The mechanism that the self-polyaddition of FTEE was initiated by the addition of radical onto the perfluoroisopropenyl group followed by a 1,5-shift to afford a methyl radical that attacked the perfluoroisopropenyl group of another FTEE molecule is proposed.",

author = "Hirotada Fujiwara and Tadashi Narita and Hiroshi Hamana",

year = "2003",

month = sep,

day = "15",

doi = "10.1002/pola.10819",

language = "English",

volume = "41",

pages = "2743--2754",

journal = "Journal of Polymer Science, Part A: Polymer Chemistry",

issn = "0887-624X",

publisher = "John Wiley and Sons Inc.",

number = "18",

}

TY - JOUR

T1 - Self-polyaddition of triethylsilyl perfluoroisopropenyl ether

AU - Fujiwara, Hirotada

AU - Narita, Tadashi

AU - Hamana, Hiroshi

PY - 2003/9/15

Y1 - 2003/9/15

N2 - The results on radical self-polyaddition reactivity of two trialkylsilyl perfluoroisopropenyl ethers, triethysilyl perfluoroisopropenyl ether [CF2=C(CF3)OSi(C2H5)3] (FTEE) and dimethylphenylsilyl perfluoroisopropenyl ether [CF2=C(CF3)OSi(CH3)2C6 H5] (DMPE), and two perfluoroisopropenyl carboxylates, 2-butyroxypentafluoropropene [CF2=C(CF3)OCOC3H7] (BuFPP) and 2-(methoxyacetoxy)pentafluoropropene [CF2=C(CF3)OCOCH2OCH3] (MFPP), are described. Radical self-polyaddition of FTEE afforded a polymer as high as 1.87 × 104 in molecular weight in the presence of radical generators such as benzoyl peroxide and di-tert-butyl peroxide. DMPE gave only addition products with initiating radicals. BuFPP and MFPP scarcely yielded even addition products with radical. The mechanism that the self-polyaddition of FTEE was initiated by the addition of radical onto the perfluoroisopropenyl group followed by a 1,5-shift to afford a methyl radical that attacked the perfluoroisopropenyl group of another FTEE molecule is proposed.

AB - The results on radical self-polyaddition reactivity of two trialkylsilyl perfluoroisopropenyl ethers, triethysilyl perfluoroisopropenyl ether [CF2=C(CF3)OSi(C2H5)3] (FTEE) and dimethylphenylsilyl perfluoroisopropenyl ether [CF2=C(CF3)OSi(CH3)2C6 H5] (DMPE), and two perfluoroisopropenyl carboxylates, 2-butyroxypentafluoropropene [CF2=C(CF3)OCOC3H7] (BuFPP) and 2-(methoxyacetoxy)pentafluoropropene [CF2=C(CF3)OCOCH2OCH3] (MFPP), are described. Radical self-polyaddition of FTEE afforded a polymer as high as 1.87 × 104 in molecular weight in the presence of radical generators such as benzoyl peroxide and di-tert-butyl peroxide. DMPE gave only addition products with initiating radicals. BuFPP and MFPP scarcely yielded even addition products with radical. The mechanism that the self-polyaddition of FTEE was initiated by the addition of radical onto the perfluoroisopropenyl group followed by a 1,5-shift to afford a methyl radical that attacked the perfluoroisopropenyl group of another FTEE molecule is proposed.

UR - http://www.scopus.com/inward/record.url?scp=0043285040&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0043285040&partnerID=8YFLogxK

U2 - 10.1002/pola.10819

DO - 10.1002/pola.10819

M3 - Article

AN - SCOPUS:0043285040

SN - 0887-624X

VL - 41

SP - 2743

EP - 2754

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

IS - 18

ER -

Self-polyaddition of triethylsilyl perfluoroisopropenyl ether

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this