Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 20
119
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

γ‐PCC and γ‐PCC‐SiO2 as Efficient Reagents for Oxidation of Thiols to Disulfides

, , &
Pages 3661-3666 | Received 12 Jan 2004, Published online: 19 Apr 2010

References

  • Palmer , B. D. , Newcastle , G. W. , Tompson , A. M. , Boyd , M. , Showalter , H. D.H. , Sercel , A. D. , Fry , D. W. , Kraker , A. J. and Denny , W. A. 1995 . Tyrosine kinase inhibitors, 4. Structure–activity relationships among N‐ and 3‐substituted 2, 2′‐dithiobis(1 H‐indoles) for in vitro inhibition of receptor and nonreceptor protein tyrosine kinases . J. Med. Chem. , 38 : 58 [PUBMED] [INFOTRIEVE] [CSA]
  • Li , K. W. , Wu , J. , Xing , W. and Simon , J. A. 1996 . total synthesis of the antitumor depsipeptide FR‐901,228 . J. Am. Chem. Soc. , 118 : 7237 [CROSSREF]
  • Sato , T. , Otera , J. and Nozaki , H. 1990 . Activation and synthetic applications of thiostannanes. Efficient conversion of thiols into disulfides . Tetrahedron Lett. , 31 : 3591 [CROSSREF]
  • Wu , X. and Rieke , R. D. 1996 . Preparation of disulfides by the oxidation of thiols using bromine . Synth. Commun. , 26 : 191
  • Noureldin , N. A. , Caldwell , M. , Hendry , J. and Lee , D. G. 1998 . Heterogeneous permanganate oxidation of thiols . Synthesis , : 1587 [CROSSREF]
  • Abele , E. , Abele , R. and Lukevics , E. 1999 . Selective and simple phase transfer catalyzed synthesis of disulfides from thiols . J. Chem. Res. (S) , : 624 [CROSSREF]
  • Movassagh , B. , Lakouraj , M. M. and Ghodrati , K. 1999 . Caro's acid supported on silica gel. Part 1: oxidative coupling of thiols to disulfides . Synth. Commun. , 29 : 3597
  • Iranpoor , N. and Zeynizadeh , B. 1999 . Air oxidative coupling of thiols to disulfides by Fe (III)/NaI . Synthesis , : 49 [CROSSREF]
  • Meshram , H. M. , Bandyopdhyay , A. , Reddy , G. S. and Yadav , J. S. 2000 . Microwave thermolysis I: A convenient and rapid coupling thiols using “clayan” in solvent free conditions . Synth. Commun. , 30 : 701
  • Kesavan , V. , Bonnet‐Delpon , D. and Begue , J.‐P. 2000 . Oxidation in fluoro alcohols: Mild and efficient preparation of disulfides from thiols . Synthesis , : 223 [CROSSREF]
  • Sanz , R. , Aguado , R. , Pedrosa , M. R. and Arnaiz , F. J. 2002 . Simple and selective oxidation of thiols to disulfides with dimethylsulfoxide catalyzed by dichlorodioxomolybdenum (VI) . Synthesis , : 856 [CROSSREF]
  • Raghavan , S. , Rajender , A. , Joseph , S. C. and Rasheed , M. A. 2001 . Catalytic oxidation of thiols to disulfides with vanadyl acetylacetonate (VO(ACAC)2) . Synth. Commun. , 31 : 1477 [CROSSREF]
  • Zeynizadeh , B. 2002 . Oxidative coupling of thiols to disulfides with iodine in wet acetonitrile . J. Chem. Res. (S) , : 564
  • Corey , E. J. and Suggs , J. W. 1975 . Pyridinium chlorochromate: An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds . Tetrahedron Lett. , 31 : 2647 [CROSSREF]
  • Guziec , F. S. Jr and Luzzio , F. A. 1980 . The oxidation of alcohols using 2,2‐bipyridinium chlorochromate . Synthesis , : 691 [CROSSREF]
  • Guziec , F. S. Jr and Luzzio , F. A. 1982 . 4‐(Dimethylamino)pyridinium chlorochromate, a new selective reagent for the oxidation of allylic and benzylic alcohols . J. Org. Chem. , 47 : 1787
  • Doad , G. J.S. 1988 . Pyrazinium chlororchromate: A new oxidizing agent . J. Chem. Res. (S) , : 270
  • Santaniello , E. , Milani , F. and Casati , R. 1983 . Tetrabutylammonium chlorochromate, a new mild and selective oxidizing agent . Synthesis , : 749 [CROSSREF]
  • Mohammadpour‐Baltork , I. and Pouranshirvani , S. 1996 . 3‐Carboxy pyridinium chlorochromate: An inexpensive and efficient reagent for cleavage of carbon–nitrogen double bonds under non‐aqueous conditions . Synth. Commun. , 26 : 1
  • Zhang , G. Sh. , Shi , Q. Z. , Chen , M. F. and Cai , K. 1997 . Ammonium chlorochromate adsorbed on alumina: A new reagent for oxidation of alcohols and benzoins to the corresponding carbonyl compounds . Synth. Commun. , 27 : 953
  • Khodaei , M. M. , Salehi , P. and Goodarzi , M. 2001 . γ‐Picolinium chlorochromate (γ‐PCC): A new and efficient reagent for the oxidation of primary and secondary alcohols . Synth. Commun. , 31 : 1253 [CROSSREF]
  • Salehi , P. , Khodaei , M. M. and Goodarzi , M. 2002 . A mild and selective deoximation method using γ‐picolinium chlorochromate (γ‐PCC) . Synth. Commun. , 32 : 1259 [CROSSREF]
  • Salehi , P. , Khodaei , M. M. and Goodarzi , M. 2002 . Oxidative deprotection of cyclic acetals and trimethylsilyl ethers by γ‐picolinium chlorochromate under nonaqueous conditions . Russ. J. Org. Chem. , 38 : 1671 [CROSSREF]
  • Salehi , P. , Farrokhi , A. and Gholizadeh , M. 2002 . Oxidative couping of thiols by pyridinium chlorochromate in solution and solvent free conditions . Synth. Commun. , 32 : 2777 [CROSSREF]
  • Raghavan , S. , Rajender , A. , Joseph , S. C. and Rasheed , M. A. 2001 . Catalytic oxidation of thiols to disulfides with vanadyl acetylacetone (VO(ACAC)2) . Synth. Commun. , 31 : 1477 [CROSSREF]

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.