Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 20
2,963
Views
23
CrossRef citations to date
0
Altmetric
Original Articles

tris(2-Carboxyethyl)phosphine (TCEP) for the Reduction of Sulfoxides, Sulfonylchlorides, N-Oxides, and Azides

&
Pages 3503-3511 | Received 17 Apr 2003, Published online: 15 Aug 2006

References

  • Levison , M.E. , Josephson , A.S. and Kirschenbaum , D.M. 1969 . Reduction of biological substances by water-soluble phosphines: gamma-globuline (IgG) . Experientia , 25 ( 2 ) : 126 – 127 .
  • Burns , J.A. , Butler , J.C. , Moran , J. and Whitesides , G.M. 1991 . Selective reduction of disulfides by tris(2-carboxyethyl)phosphines . J. Org. Chem. , 56 ( 8 ) : 2648 – 2650 .
  • Getz , E.B. , Xiao , M. , Chakrabarty , T. , Cooke , R. and Selvin , P.R. 1999 . A comparison between the sulfhydryl reductants tris(2-carboxyethyl)phosphine and dithiothreitol for use in protein biochemistry . Anal. Biochem. , 273 ( 1 ) : 73 – 80 .
  • Sack , R. , Willi , A. and Hunziker , P.E. 2000 . Determination of total glutathione in cell lysates by high performance liquid chromatography with O-phthalaldehyde precolumn derivatization in the presence of tris(2-carboxyethyl)phosphine . J. Liq. Chromatogr. Relat. Technol. , 23 ( 19 ) : 2947 – 2962 . For example: (a)
  • Han , J. , Chu , T.-C. , Han , G. , Browne , J. , Brown , I. and Han , P. 1998 . Spectrophotometric assay for hypochlorite/hypochlorous acid using tris(2-carboxyethyl) phosphine . Microchem. J. , 58 ( 2 ) : 218 – 224 .
  • Han , J. , Payne , V. , Yen , S. , Han , G. and Han , P. 1996 . Use of tris(2-carboxyethyl)phosphine for Quantitation of Iodine and Iodate . Anal. Biochem. , 242 ( 1 ) : 150 – 152 .
  • Drabowicz , J. , Togo , H. , Mikolajczyk , M. and Oae , S. 1984 . Reduction of sulfoxides . A review. Org. Prep. Proc. Int. , 16 ( 3–4 ) : 171 – 198 . and references cited therein
  • Madesclaire , M. 1988 . Reduction of sulfoxides to thioethers . Tetrahedron , 44 ( 21 ) : 6537 – 6580 . and references cited therein
  • Katritzky , Lagowski. 1971 . Chemistry of the Heterocyclic N-Oxides 166 – 231 . New-York : Academic Press Inc. .
  • Olah , G.A. , Gupta , B.G.B. and Narang , S.C. 1978 . Synthetic methods and reactions. 54. Deoxygenation of sulfoxides and azoxides with tris(dimethylamino)phosphine/iodine/sodium iodide reagent . Synthesis , : 137 – 138 .
  • Olah , G.A. , Gupta , B.G.B. and Narang , S.C. 1978 . Synthetic methods and reactions. 45. Deoxygenation of sulfoxides with triphenylphosphine/iodine/sodium iodide reagent . Synthesis , : 137 – 138 .
  • Fujimori , K. , Togo , H. and Oae , S. 1980 . Iodine catalyzed reduction of arenesulfonic acid to the arenethiol with triphenylphosphine . Tet. Lett. , 21 : 4921 – 4924 .
  • Oae , S. and Togo , H. 1981 . Biomimetic reduction of sulfuric acid . Chem. Letters , : 1387 – 1390 .
  • Oae , S. and Togo , H. 1983 . Reduction of sulfonic acids and related organosulfur compounds with triphenylphosphine-iodine system . Bull. Chem. Soc. Jpn. , 56 ( 12 ) : 3802 – 3812 .
  • Barton , D.H. , Fekih , A. and Lusinchi , X. 1985 . Selective reduction of the N-O bond in N-Oxides and in nitrones by sodium hydrogene telluride . Tet. Lett. , 26 ( 38 ) : 4603 – 4606 .
  • Handa , Y. , Inanaga , J. and Yamaguchi , M. 1989 . Rapid and mild deoxygenation of organoheteroatom oxides with the efficient electron transfer system SmI2-tetrahydrofuran-hexamethylphosphoric triamide . J. Chem. Soc., Chem. Commun. , : 298 – 299 .
  • Nicolaou , K.C. , Koumbis , A.E. , Snyder , S.A. and Simonsen , K.B. 2000 . Novel reactions initiated by titanocene methylidenes: deoxygenation of sulfoxides, N-oxides, and selenoxides . Angew. Chem. Int. Ed. , 39 ( 14 ) : 2529 – 2533 .
  • Staudinger , H. and Meyer , J. 1919 . New organic compounds of phosphorus. III. Phosphinemethylene derivatives and phosphinimines . Helvetica Chim. Acta , 2 : 635 – 646 .
  • Knouzi , N. , Vaultier , M. and Carrie , R. 1985 . Reduction of azides by triphenylphosphine in the presence of water: a general and chemoselective access to primary amines . Bull. Chem. Soc Fr. , : 815 – 819 .

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.