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Synthesis 2010(11): 1883-1890  
DOI: 10.1055/s-0029-1218785
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Syntheses of Mono-, Di-, and Trifluorinated Styrenic Monomers

Justyna Walkowiaka, Teresa Martinez del Campoa, Bruno Amedurib, Véronique Gouverneur*a
a Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK
b Institut Charles Gerhardt, Ingénierie et Architectures Macromoléculaires, UMR CNS 5253, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l’Ecole Normale, 34296 Montpellier, France
Fax: +44(1865)275644; e-Mail: veronique.gouverneur@chem.ox.ac.uk;
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Publikationsverlauf

Received 29 April 2010
Publikationsdatum:
12. Mai 2010 (online)

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Abstract

Concise syntheses of gram quantities of three fluorinated α-methylstyrenic monomers suitable for polymerisation studies are disclosed, all based on the use of reasonably priced commercially available starting materials and reagents.

Key words

fluorination - nucleophilic fluoroalkylation - palladium catalysis - monomer synthesis - functional fluoropolymers

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20

Trimethyl[difluoro(phenyl)methylsulfonyl]silane was observed in the crude mixture as a major product along with traces of sulfone 17. Notably, purification on Biotage (Biotage KP-SIL SNAP Flash Cartridges) resulted in the recovery of sulfone 17, suggesting that desilylation occurred upon purification.