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Telomerisation Reactions of fluorinated alkenes

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Organofluorine Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 192))

Abstract

The synthesis of fluorinated oligomers by radical telomerisation of fluoroalkenes is discussed. After a brief presentation of the various parameters which direct this reaction and the kinetic laws, this review outlines the traditional telogens efficient in telomerisation and also considers other transfer agents which undergo less known cleavages. Telomerisation involving main fluorinated alkenes (vinylidene fluoride, tetrafluoroethylene, chlorotrifluoroethylene, trifluoroethylene and hexafluoropropene) and less used agents is then reviewed, considering either the method of initiation including new activation systems, or specific cleavage of the telogens used. Some examples of cotelomerisation are given constituting interesting models of copolymerisation. General concepts of reactivity regarding the orientation of addition of free radicals to unsymmetrical fluorinated alkenes and also comparison of the reactivity of various fluorinated alkenes with the telogens are discussed and several examples given. Beside the traditional process of telomerisation, the living telomerisation methods are also described. In these methods, the living character is mentioned and well chosen transfer agents with specific cleavable bonds described. The living behaviour of the iodine transfer polymerisation or stepwise cotelomerisation occurs in the presence of perfluoroalkyl iodides or α, ω-diiodoperfluoroalkanes as the telogens and shows high interest in the synthesis of structurally well defined telomers. Finally, the application of fluoropolymers synthesised from these telomers is presented showing the high added value of these materials.

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Abbreviations

AIBN:

azobisisobutyronitrile

BEPH:

butyl ethyl peroxyhexanoate

BDE:

bond dissociation energy

Bu:

n-butyl

tBu:

tertio-butyl

CR:

counter radical

CT :

transfer constant

CTFE:

chlorotrifluoroethylene

d:

day

DBP:

dibenzoyl peroxide

DIPC:

diisopropyl peroxydicarbonate

DPn :

average degree of polymerisation in number

DTBP:

ditertio-butyl peroxide

F113:

1,1,2-trifluorotrichloroethane

HFPO:

hexafluoropropylene oxide

iPr:

isopropyl

IRFI:

α, ω-diiodoperfluoroalkane

ITP:

iodine transfer polymerisation

M:

monomer

[M]:

concentration of monomer

Mn :

average molecular weight in number

Mω :

average molecular weight in weight

NMR:

nuclear magnetic resonance

PCTFE:

poly(chlorotrifluoroethylene)

PHFP:

poly(hexafluoropropene)

PTFE:

poly(tetrafluoroethylene)

PVDF:

poly(vinylidene fluoride)

PVF:

poly(vinyl fluoride)

R:

alkyl radical

R:

alkyl group

RF :

perfluorinated group

RF,Cl :

chlorofluorinated group

RFBr:

perfluoroalkyl bromide

RFI:

perfluoroalkyl iodide

RT:

room temperature

sc:

supercritical

Tempo:

2,2,6,6-tetramethyl piperidinyl-1-oxyl

TFE:

tetrafluoroethylene

Tg:

glass transition temperature

THF:

tetrahydrofuran

UV:

ultra violet

VDF:

vinylidene fluoride

VF:

vinyl fluoride

Δ:

heating

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  1. ESA 5076 (CNRS) Ecole Nationale Supérieure de Chimie de Montpellier 8, Rue Ecole Normale, F-34296, Montpellier Cedex 5, France

    Bruno Améduri & Bernard Boutevin

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  1. Bruno Améduri
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  2. Bernard Boutevin
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Richard D. Chambers

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Améduri, B., Boutevin, B. (1997). Telomerisation Reactions of fluorinated alkenes. In: Chambers, R.D. (eds) Organofluorine Chemistry. Topics in Current Chemistry, vol 192. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0119267

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