Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 4
51
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis and Pummerer Reaction of α,ω‐Bis(Fluoroalkylsulfinylmethyl)Polyethylene Glycols

, &
Pages 543-556 | Received 30 Jun 2004, Published online: 12 Apr 2011

References

  • Watanabe , Y. , Numata , T. and Oae , S. 1981 . Mild and facile preparation of sulfoxides from sulfides using titanium (III) chloride/hydrogen peroxide . Synthesis , : 204 – 206 .
  • Hilda , B. , Brink , T. , Herbert , L. H. , Schoemaker , E. S. , Lingen , H. and Wever , R. 1999 . Probing the scope of the sulfoxidation activity of vanadium bromoperoxidase from Ascophyllum nodosum . Tetrahedron: Asymmetry , 10 : 4563 – 4565 .
  • Mashraqui , H. , Chandrasekar , D. and Mudaliar and Madhavi , A. 1998 . Bio(NO3)3 · 5H2O: A convenient reagent for selective oxidation of sulfides to sulfoxides . Synth. Commun. , 28 : 939 – 943 .
  • Vetter , H. and Berkessel , A. 1998 . Schiff‐base ligands carrying two elements of chirality: Matched‐mismatched effects in the vanadium‐catalyzed sulfoxidation of thioethers with hydrogen peroxide . Tetrahedron Lett. , 39 : 1741 – 1744 .
  • Colonna , S. , Gaggero , N. , Casella , L. , Carrea , G. and Pasta , P. 1992 . Chloroperoxidase and hydrogen peroxide: An efficient system for enzymatic enantioselective sulfoxidations . Tetrahedron: Asymmetry , 3 : 95 – 106 .
  • Massa , A. , Lanttanzi , A. , Sinisclchi , F. R. and Scettri , A. 2001 . Catalytic enantioselective oxidation of sulfides to sulfoxides with a renewable hydroperoxide . Tetrahedron: Asymmetry , 12 : 2775 – 2777 .
  • Ravikumar , K. S. , Bégué , J. P. and Bonnet‐Delpon , D. 1998 . A selective conversion of sulfide to sulfoxide in hexafluoro‐2‐propanol . Tetrahedron Lett. , 39 : 3141 – 3144 .
  • Palombi , L. , Bonadies , F. , Pazienza , A. and Scettri , A. 1998 . A convenient approach to chiral sulfoxides by enantioselective oxidation with a steroïdal furylhydroperoxide . Tetrahedron: Asymmetry , 9 : 1817 – 1822 .
  • Treiber , A. 2002 . Mechanism of the aromatic hydroxylation of thiophene by acid‐catalyzed peracid oxidation . J. Org. Chem. , 67 : 7261 – 7266 .
  • Shaabani , A. , Ben Teimouri , M. and Safaei , H. R. 2000 . A simple and efficient procedure for oxidation of sulfides to sulfoxides by hexamethylenetetramine‐bromine complex(HMTAB) . Synth. Commun. , 30 : 265 – 271 .
  • Firouzabadi , H. , Iranpoor , N. and Zolfigol , M. A. 1998 . Selective and efficient transformation of thioethers to their sulfoxides and catalytic conversion of thiols to the disulfides with hydrated iron(III) and copper(II) nitrates in aprotic organic solvents or under solvent free conditions . Synth. Commun. , 28 : 1179 – 1187 .
  • Iriuchijima , S. , Maniwa , K. and Tsuchihashi , G. 1974 . Organic synthesis by the pummerer reaction. I. Synthesis of α‐hydroxyaldehydes from β‐hydroxy sulfoxides . J. Am. Chem. Soc. , 96 : 4280 – 4283 .
  • Iriuchijima , S. , Maniwa , K. and Tsuchihashi , G. 1976 . Synthesis of α‐hydroxy aldehyde and α‐hydroxy acid derivatives from β‐hydroxy or β‐oxo sulfoxides . Agr. Biol. Chem. , 40 : 2389 – 2396 .
  • Yoshimitsu , N. , Satoshi , M. , Kazuhiko , H. , Ado , M. and Shigeki , S. 2002 . Highly chemoselective pummerer reactions of sulfinyldiacetic acid derivative . Tetrahedron Lett. , 43 : 1519 – 1522 .
  • Grayaa Jaoued , N. and Hedhli , A. 2003 . Synthesis of highly fluorinated nonionic surfactants . J. Disp. Scien. and Tech. , 24 : 6749 – 753 .
  • Hedhli , A. , Szonyi , S. , Baklouti , A. and Cambon , A. 1994 . Synthesis and pummerer reaction of 2‐F‐alkyl‐2‐hydroxyethylphenyl sulfoxides . J. Fluorine Chem. , 69 : 133 – 138 .
  • Hedhli , A. and Baklouti , A. 1996 . La Reaction de Pummerer: Aspects et Applications . J. Soc. Chim. Tunisie , II : 847 – 862 .
  • Aroua , L. , Hedhli , A. and Baklouti , A. 1999 . Hydrofluorination of oligoethylene glycol diglycidyl ethers . Synthesis , : 85 – 89 .

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.