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
References
<A NAME="RC02810SS-1A">1a </A>
Wall LA.
Fluoropolymers
Wiley;
New
York:
1972.
<A NAME="RC02810SS-1B">1b </A>
Feiring AE. In Organofluorine Chemistry:
Principles and Commercial Applications
Banks RE.
Smart BE.
Tatlow JC.
Plenum
Press;
New York:
1994.
Chap. 15.
p.339-372
<A NAME="RC02810SS-1C">1c </A>
Scheirs J.
Modern Fluoropolymers
Wiley;
New
York:
1997.
<A NAME="RC02810SS-1D">1d </A>
Hougham G.
Davidson T.
Cassidy P.
Johns K.
Fluoropolymers
Kluvert;
New
York:
1999.
<A NAME="RC02810SS-1E">1e </A>
Ameduri B.
Boutevin B.
Well
Architectured Fluoropolymers: Synthesis, Properties and Applications
Elsevier;
Amsterdam:
2004.
<A NAME="RC02810SS-2A">2a </A>
Kobayashi S,
Munekuta S,
Unoki M, and
Iwamoto T. inventors; Patent
EP 0239935.
<A NAME="RC02810SS-2B">2b </A>
Yamamoto T,
Matsumoto T,
Shimada K,
Uozu Y, and
Murata R. inventors; Patent
EP 0256765.
<A NAME="RC02810SS-2C">2c </A>
Skutnik BJ. inventors; Patent AU 569145.
<A NAME="RC02810SS-2D">2d </A>
Yamamoto S, and
Matsumoto M. inventors; Patent JP 63430104.
<A NAME="RC02810SS-3">3 </A>
Boutevin B.
Pietrasanta Y.
Les
Acrylates et poly Acrylates fluorés
Erec;
Paris:
1998.
<A NAME="RC02810SS-4">4 </A>
Banks BA.
The Use of Fluoropolymers in Space Applications,
Modern Fluoropolymers
Wiley;
New
York:
1999.
Chap. 4.
p.103-114
<A NAME="RC02810SS-5A">5a </A>
Souzy R.
Ameduri B.
Boutevin B.
J. Polym. Sci., Part A: Polym.
Chem.
2004,
42:
5077
<A NAME="RC02810SS-5B">5b </A>
Kostov G.
Tredwell M.
Ameduri B.
Gouverneur V.
J. Poly. Sci., Part A: Polym.
Chem.
2007,
45:
3843
<A NAME="RC02810SS-6A">6a </A>
Olofsson K.
Larhed M.
Hallberg A.
J. Org. Chem.
1998,
63:
5076
<A NAME="RC02810SS-6B">6b </A>
Tredwell M.
Gouverneur V.
Org. Biomol. Chem.
2006,
4:
26
<A NAME="RC02810SS-6C">6c </A>
Nyffeler PT.
Duron SG.
Burkart MD.
Vincent SP.
Wong C.-H.
Angew. Chem. Int. Ed.
2005,
44:
192
<A NAME="RC02810SS-7">7 </A>
Mo J.
Xu L.
Xiao J.
J. Am. Chem.
Soc.
2005,
127:
751
<A NAME="RC02810SS-8">8 </A>
Luo H.-Q.
Loh T.-P.
Tetrahedron Lett.
2009,
50:
1554
<A NAME="RC02810SS-9A">9a </A>
Mo J.
Xu L.
Ruan J.
Liu S.
Xiao J.
Chem.
Commun.
2006,
3591
<A NAME="RC02810SS-9B">9b </A>
Pei W,
Sun L, and
Xiao J. inventors; Patent
CN 1,634,825.
<A NAME="RC02810SS-10">10 </A>
Organ MG.
Murray AP.
J. Org. Chem.
1997,
62:
1523
<A NAME="RC02810SS-11">11 </A>
Bresciani S.
Slawin AMZ.
O’Hagan D.
J. Fluorine Chem.
2009,
130:
537
<A NAME="RC02810SS-12A">12a </A>
Kotov SV.
Pedersen SD.
Qiu W.
Qiu Z.-M.
Burton DJ.
J. Fluorine Chem.
1997,
82:
13
<A NAME="RC02810SS-12B">12b </A>
Stone C.
Daynard TS.
Hu L.-Q.
Mah C.
Steck AE.
J.
New Mater. Electrochem. Syst.
2000,
3:
43
<A NAME="RC02810SS-12C">12c </A>
Lafitte B.
Jannasch P.
On the Prospects for Phosphonated
Polymers as Proton-Exchange Fuel Cell Membranes, In Advances in Fuel
Cells
Zhao T.
Kreuer K.-D.
Van Nguyen T.
Elsevier;
Amsterdam:
2007.
Chap.
3.
<A NAME="RC02810SS-13A">13a </A>
Ohmori H.
Nakai S.
Masui M.
J. Chem. Soc., Perkin Trans. 1
1979,
2023
<A NAME="RC02810SS-13B">13b </A>
Obrycki R.
Griffin CE.
J. Org. Chem.
1968,
33:
632
<A NAME="RC02810SS-13C">13c </A>
Plumb JB.
Obrycki R.
Griffin CE.
J. Org. Chem.
1966,
31:
2455
<A NAME="RC02810SS-14A">14a </A>
Balthazor TM.
Grabiak RC.
J. Org. Chem.
1980,
45:
5425
<A NAME="RC02810SS-14B">14b </A>
Tavs P.
Chem.
Ber./Recl
1970,
103:
2428
<A NAME="RC02810SS-15A">15a </A>
Schwan AL.
Chem. Soc. Rev.
2004,
33:
218
<A NAME="RC02810SS-15B">15b </A>
Hirao T.
Masunaga T.
Yamada N.
Ohshiro Y.
Agawa T.
Bull.
Chem. Soc. Jpn.
1982,
55:
909
<A NAME="RC02810SS-16A">16a </A>
Burger A.
Dawson ND.
J.
Org. Chem.
1951,
16:
1250
<A NAME="RC02810SS-16B">16b </A>
Dawson ND.
Burger A.
J. Org. Chem.
1953,
18:
207
<A NAME="RC02810SS-16C">16c </A>
Eymery F.
Iorga B.
Savignac P.
Tetrahedron
1999,
55:
13109
<A NAME="RC02810SS-17A">17a </A>
Organofluorine Compounds. Chemistry and Applications
Hiyama T.
Springer;
New
York:
2000.
<A NAME="RC02810SS-17B">17b </A>
Organofluorine
Chemistry - Principles and Commercial Applications
Banks RE.
Smart BE.
Tatlow JC.
Plenum
Press;
New York:
1994.
<A NAME="RC02810SS-17C">17c </A>
Fluorine
in Bioorganic Chemistry
Welch JT.
Eshwarakrishman S.
Wiley;
New
York:
1991.
<A NAME="RC02810SS-17D">17d </A>
Fluorine-Containing
Molecules. Structure, Reactivity, Synthesis, and Applications
Liebman JF.
Greenberg A.
Dolbier WR.
VCH;
New York:
1988.
<A NAME="RC02810SS-18A">18a </A>
Shimazu M.
Maeda T.
Fujisawa T.
J. Fluorine Chem.
1995,
71:
9
<A NAME="RC02810SS-18B">18b </A>
Kuroboshi M.
Hiyama T.
J. Fluorine Chem.
1994,
69:
127
<A NAME="RC02810SS-18C">18c </A>
Hugenberg V.
Haufe G.
Synlett
2008,
106
<A NAME="RC02810SS-18D">18d </A>
Hiyama T, and
Kuroboshi M. inventors; Patent JP 4264041.
<A NAME="RC02810SS-19A">19a </A>
Burton DJ.
Wiemers DM.
J. Fluorine Chem.
1981,
18:
573
<A NAME="RC02810SS-19B">19b </A>
Li X.-Y.
Jiang X.-K.
Gong Y.-F.
Pan H.-Q.
Acta Chim. Sin. (Engl. Ed.)
1985,
43:
260
<A NAME="RC02810SS-19C">19c </A>
Prakash GKS.
Hu J.
Olah GA.
J. Org. Chem.
2003,
68:
4457
<A NAME="RC02810SS-20">20 </A>
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.
<A NAME="RC02810SS-21A">21a </A>
Prakash GKS.
Hu J.
Wang Y.
Olah GA.
Eur.
J. Org. Chem.
2005,
2218
<A NAME="RC02810SS-21B">21b </A>
Ni C.
Hu J.
Tetrahedron Lett.
2005,
46:
8273
<A NAME="RC02810SS-22">22 </A> When reductive desulfonation was
performed prior to the dehydration, compound 17 was
observed, but it was contaminated by significant amount of inseparable byproduct.
Kazennikova GV.
Talalaeva TV.
Zimin AV.
Kocheshkov KA.
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk
1961,
6:
1060
<A NAME="RC02810SS-23">23 </A>
Gøgsig TM.
Søbjerg LS.
Lindhardt AT.
Jensen KL.
Skrydstrup T.
J. Org.
Chem.
2008,
73:
3404
<A NAME="RC02810SS-24">24 </A>
Jiang B.
Xu Y.
Tetrahedron Lett.
1992,
33:
511
<A NAME="RC02810SS-25">25 </A>
Pan R.-q.
Liua X.-x.
Deng M.-z.
J.
Fluorine Chem.
1999,
95:
167