Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 7
217
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Direct Perfluorination of an Acid-Sensitive Glycol Ether as Precursor for Perfluoro(2-(methoxymethoxy)ethyl Vinyl Ether)

, , , , , , , , , & show all
Pages 959-966 | Received 23 Apr 2010, Published online: 16 Dec 2011

REFERENCES

  • Sianesi , D. ; Marchionni , G. ; DePasquale , R. J. In Organofluorine Chemistry: Principles and Commercial Applications ; R. E. Banks , B. E. Smart , J. C. Tatlow (Eds.); Plenum Press : New York , 1994 ; pp. 431 – 461 .
  • Carlson , D. P. ; Schmiegel , W. In Ullmann's Encyclopedia of lndustrial Chemistry ; VCH Publishers : 1988 ; Weinheim.
  • Coggio , W. D. ; Grootaert , W. M. A. ; Hintzer , K. ; Marz , F. ; Pallarino , R. V. ; Van Gool , G. ; Worm , A. T. ; Hare , E. D. Curable perfluoro elastomers having low glass transition temperature and method of making them . WO Patent 2002060968, 2002 .
  • (a) Hintzer , K. ; Löhr , G. In Modern Fluoropolymers ; J. Scheirs (Ed.); John Wiley & Sons : Chichester , 1997 , 223 – 237 ; (b) Hiyanma , T. Organofluorine Compounds ; Springer : Berlin , 2000 ; pp. 212 – 233 .
  • Resnick , P. R. Perfluorovinyl ethers . US Patent 3692843, 1972 .
  • Navarrini , W. ; Tortelli , V. ; Russo , A. ; Corti , S. Organic hypofluorites and their new role in industrial fluorine chemistry . J. Fluorine Chem. 1999 , 95 , 27 – 39 .
  • Navarrini , W. ; Corti , S. New perfluorovinylethers through the bis(fluoroxy)difluoromethane (BDM) chemistry. J. Fluorine Chem. 2004 , 125 ( 2 ), 189 – 197 .
  • Fritz , C. G. ; Selman , S. (E. I. du Pont de Nemours and Company), U. S. Patent 3,291,843, 1966; Chem. Abstr. 1967, 66, 37427.
  • Sandford , G. Elemental fluorine in organic chemistry (1997–2006) . J. Fluorine Chem. 2007 , 128 , 90 – 104 .
  • Hung , M.-H. ; Rozen , S. ; Smart , B. E. Synthesis of perfluorovinyl ether monomers . J. Org. Chem. 1994 , 59 , 4332 – 4335 .
  • Worm , A. T. ; Moore , G. G. I. ; Guerra , M. A. ; Schwertfeger , W. ; Hintzer , K. ; Qui , Z.-M. ; Hare , E. D. Perfluorinated vinyl ethers and their manufacture . WO Patent 2001046107, 2001 .
  • Lousenberg , R. D. ; Shoichet , M. S. Synthesis of trifluorovinyl ethers incorporating functionalized hydrocarbon ether groups: Insight into the mechanism of trifluorovinyl ether formation from trimethylsilyl 2-alkoxy-2,3,3,3-tetrafluoropropionates . J. Org. Chem. 1997 , 62 , 7844 – 7849 .
  • Marchionni , G. ; Patto , U. D. ; Spataro , G. ; Tortelli , V. Synthesis of low-molecular-weight perfluoro oxymethylene vinyl ethers . J. Fluorine Chem. 2003 , 119 , 83 – 88 .
  • Process for preparing fluorine and oxygen-containing organic compounds, and products obtainable by the process. British Patent 1097679, 1968 .
  • Romano , R. M. ; Czarnowski , J. ; Della Védova , C. O. Preparation and conformational properties of the perfluoro diether CF3OCF2OCF2C(O)F, a model molecule to study properties of perfluoro polyethers . Inorg. Chem. 2001 , 40 , 3039 – 3047 .
  • Bartels , B. ; Garcia-Yebra , C. ; Rominger , F. ; Helmchen , G. Iridium-catalysed allylic substitution: Stereochemical aspects and isolation of IrIII complexes related to the catalytic cycle . Eur. J. Inorg. Chem. 2002 , 2569 – 2586 .
  • Schelhaas , M. ; Waldmann , H. Protecting group strategies in organic synthesis . Angew. Chem., Int. Ed. 1996 , 35 , 2056 – 2083 .
  • Thomas , R. Bierschenk ; Timothy , J. Juhlke ; Richard , J. Lagow. Perfluorination of ethers in the presence of hydrogen fluoride scavengers. U.S. Patent 4,755,567 , 1988 .
  • Adcock , J. L. ; Beh , R. A. ; Lagow , R. J. Successful direct fluorination of oxygen-containing hydrocarbons . J. Org. Chem. 1975 , 40 , 3271 .
  • Okazoe , T. ; Watanabe , K. ; Itoh , M. ; Shirakawa , D. ; Kawahara , K. ; Tatematsu , S. Synthesis of perfluorinated carboxylic acid membrane monomers by utilizing liquid-phase direct fluorination . J. Fluorine Chem. 2005 , 126 , 521 – 527 (reference cited therein).
  • Chambers , R. D. ; Joel , A. K. ; Rees , A. J. Elemental fluorine Part 11 [1]. Fluorination of modified ethers and polyethers . J. Fluorine Chem. 2000 , 101 , 97 – 105 .
  • Murata , K. ; Kawa , H. ; Lagow , R. J. The thermal decomposition of perfluoroesters . J. Am. Chem. Soc. 1998 , 120 , 7117 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.