Triethylammonium halochromates/silica gel: an efficient reagent for oxidative coupling of thiols to disulfides

Shahriare Ghammamy, Mohammad Kazem Mohammadi, Ali Hassani Joshaghani


Triethylammonium halochromates, (C2H5)3NCrO3X, TEAXC (X = Cl, F) are easily synthesized by the reaction of triethylamine with a solution of chromium(VI) oxide in 6M hydrochloric acid, or a solution of chromium(VI) oxide in 40% hydrofluoric acid. These reagents are easily supported on common silica gel and can be used as heterogeneous oxidants. Triethylammonium halochromate(VI) is a versatile reagent for the effective and selective oxidation of organic substrates. Various aliphatic (cyclic and acyclic) and aromatic thiols are converted into the corresponding disulfides by treatment with triethylammonium fluorochromate(VI), (TEACC) or triethylammonium chlorochromate(VI), (TEAFC) supported on silica gel, in excellent yields and under mild reaction conditions.


triethylammonium fluorochromate(VI); triethylammonium chlorochromate(VI); heterogeneous oxidants; silica gel; oxidation; thiol; disulfides

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G. Capozzi, G. Modena, S. Patai, The Chemistry of the Thiol Group, Wiley, New York, 1974, p. 785.

D. L. Holbrook, Handbook of Petroleum Refining Processes, Chap. 11.3, R.A. Meyers (Ed.), McGraw Hill, 1996.

K. -T. Liu, Y. C. Tong, A Facile Conversion of Thiols to Disulfides. Synthesis, 669 (1978).

T. J. Wallace, Reactions of Thiols with Sulfoxides. I. Scope of the Reaction and Synthetic Applications. J. Am. Chem. Soc., 86 (10), 2018–2021 (1964).

J. Choi , N. M. Yoon, Synthesis of Disulfides by Copper- Catalyzed Disproportionation of Thiols. J. Org. Chem., 60 (11), 3266 (1995).

M. Hirano, S. Yakabe, H. Monobe, T. Marimoto, Alumina: an Efficient and Reusable Catalyst for the Oxidative Coupling of Thiols with DMSO. J. Chem. Res. (S), 472 (1998).

E. Abele, R. Abele, E. Lukevics, Selective and Simple Phase Transfer Catalyzed Synthesis of Disulfides from Thiols, J. Chem. Research (S), 624 –625 (1999).

M. Hirano, S. Yakabe, K. Ando, T. Morimoto, Simple Oxidation of Thiols with Sodium Iodate under Solid– Solution Biphasic Conditions. J. Chem. Res. (S), 816 (1998).

E. J. Corey, D. L. Boger, Oxidative cationic cyclization reactions effected by pyridinium chlorochromate , Tetrahedron Lett., 19 (28) , 2461–2464 (1978).

M. N. Bhattacharjee, M. K. Chauduri, H. S. Dasgupta, Pyridinium fluorochromate; A New and Efficient Oxidant for Organic Substrates, Synthesis 588–590 (1982).

G. S. Chaubey, S. Das, M. K. Mahanti, Quinolinium dichromate oxidation of aliphatic aldehydes: A kinetic study, Croatica Chemica Acta, 76 (4), 287–291 (2003).

F. S. Guziec, F. A. Luzzio, The oxidation of alcohols using 2,2'-bipyridinium chlorochromate, Synthesis., 691– 694 (1980).

G. F. Jeyanthi, G. Vijayakumar, K. P. Elango, The effect of solvent on the benzaldehydes by quinolinium chlorochromate in aqueous organic solvent media. J. Serb. Chem. Soc. 67 (12), 803–808 (2002).

R. Srinivasan, P. Stanley, K. Balasubramanian, Isoquinolinium fluorochromate: A new and efficient oxidant for organic substrates, Synth. Commun., 27 (12) , 2057–2064 (1997) .

A. R Mahjoub, S. Ghammami, M. Z Kassaee, Tetramethylammonium fluorochromate(VI): A new and efficient 4555–4557 (2003).

Sh. Ghammamy, H. Eimanieh, M. K. Mohammady, Cetyltrimethylammonium Bromochromate: A New and Efficient Oxidant for Organic Substrates, Synth Commun., 37, 599–605 (2007).

Aldrich Catalog Handbook of Fine Chemicals, 1996– 1997, pp. 1159.

M. Montazerozohori, S. Joohari, B. Karami N. Haghighat, Fast and Highly Efficient Solid State Oxidation of Thiols, Molecules, 12, 694–702 (2007).

K. Nakamoto, Part II, Inorganic Compounds, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 3rd, Vol. 1, pp 140–150, John Wiley & Sons: New York, 1978.

M. A. Walters , J. Chaparro, T. Siddiqui, F. Williams, C. Ulku, A. L Rheingold, The Formation of Disulfides by the

[Fe(nta) Cl2]2 – Catalyzed Air Oxidation of Thiols and Dithiols, Inorg. Chimica Acta., 359, 3996–4000 (2006).

S. Patel, B. K. Mishra, Chromium(VI) Oxidants Having Quaternary Ammonium Ions: Studies on Synthetic Applications and Oxidation Kinetics, Tetrahedron, 63, 4367– 4406 (2007).



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