General, fast, and high yield oxidation of thiols and disulfides to sulfonic and sulfinic acids using HOF·CH3CN

Tetrahedron Letters

Volumn 48, Issue 46, 2007, Pages 8178-8181

  Shefer, Neta ^a   Carmeli, Mira ^a   Rozen, Shlomo ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

HOF CH3CN; Oxidation; Sulfinic acid; Sulfonic acid

Indexed keywords

ACETONITRILE DERIVATIVE; DISULFIDE; FLUORINE DERIVATIVE; SULFINIC ACID DERIVATIVE; SULFONIC ACID DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; METHODOLOGY; OXIDATION; REACTION TIME; SYNTHESIS;

EID: 35348835925     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.083     Document Type: Article

References (36)

1. Weberndoerfer, V.; Brunnmueller, F.; Eisert, M.; Bermes, R. U.S. Patent 4,560,745, 1985; Chem. Abstr. (for the appl.) 1982, 96, 574.
2. Tian S.H., Shu D., Wang S.J., Xiao M., and Meng Y.Z. Fuel Cells 7 (2007) 232-237
3. Boesten, W. H. J.; Quaedflieg, P. J. L. M. PCT Int. Appl. WO 9849133, 1998; Chem. Abstr. 1998, 129, 739.
4. Levene P.A., and Mikeska L.A. J. Biol. Chem. 75 (1927) 587-605
5. Levene P.A., and Mikeska L.A. J. Biol. Chem. 65 (1925) 515-518
6. Vivian D.L., and Reid E.E. J. Am. Chem. Soc. 57 (1935) 2559-2560
7. Cerfontain H., Lambrechts H.J.A., Schaasberg Z.R.H., Coombes R.G., Hadjigeorgion P., and Tucker G.P. J. Chem. Soc., Perkin Trans. 2 (1985) 659-667
8. 2O in a regular glass reactor. The development of the oxidizing power was monitored by reacting aliquots with an acidic aqueous solution of KI. The liberated iodine was then titrated with thiosulfate. The typical concentrations of the oxidizing reagent were around 0.4-0.6 mol/L.
9. Rozen S., and Bareket Y. J. Org. Chem. 62 (1997) 1457-1462
10. Rozen S., and Bareket Y. J. Chem. Soc., Chem. Commun. (1994) 1959
11. Harel T., Amir E., and Rozen S. Org. Lett. 8 (2006) 1213-1216
12. Amir E., and Rozen S. Angew. Chem., Int. Ed. 44 (2005) 7374-7378
13. Rozen S., and Carmeli M. J. Am. Chem. Soc. 125 (2003) 8118-8119
14. Carmeli M., and Rozen S. J. Org. Chem. 71 (2006) 4585-4589
15. Golan E., and Rozen S. J. Org. Chem. 68 (2003) 9170-9172
16. Dayan S., Kol M., and Rozen S. Synthesis (1999) 1427-1430
17. Rozen S., and Dayan S. Angew. Chem., Int. Ed. 38 (1999) 3471-3473
18. Rozen S., and Carmeli M. J. Org. Chem. 70 (2005) 2131-2134
19. Rozen S. Eur. J. Org. Chem. (2005) 2433-2447
20. Rozen S. Acc. Chem. Res. 29 (1996) 243-248
21. 13C NMR at 50 and 100 MHz. The IR spectra were recorded in KBr on an FTIR spectrophotometer. The MS were measured under CI or EI conditions. The spectral and physical properties of known products were compared with those reported in the literature. In every case excellent agreement was obtained.
22. Smith K., and Hou D. J. Org. Chem. 61 (1996) 1530-1532
23. Freeman F., and Angeletakis C.N. Org. Magn. Reson. 21 (1983) 86-93
24. Loew O.G. J. Org. Chem. 41 (1976) 2061-2064
25. Ishii Y., Matsunaka K., and Sakaguchi S. J. Am. Chem. Soc. 122 (2000) 7390-7391
26. Ferguson R.R., and Crabtree R.H. J. Org. Chem. 56 (1991) 5503-5510
27. Stone G.C.H. J. Am. Chem. Soc. 58 (1936) 488-489
28. Wallace T.J., and Schriesheim A. Tetrahedron 21 (1965) 2271-2280
29. Kol M., and Rozen S. J. Org. Chem. 58 (1993) 1593-1595
30. Zoller, U. In The Chemistry of Sulphinic Acids, Esters and their Derivatives. Patai, S., Ed.; 1990; pp 185-215.
31. Gu D., and Harpp D.N. Tetrahedron Lett. 34 (1993) 67-70
32. 19b
33. Nambu H., Hata K., Matsugi M., and Kita Y. Chem. Eur. J. 11 (2005) 719-727
34. Umemoto T., and Tomizawa G. J. Org. Chem. 60 (1995) 6563-6570
35. Filby W.G., Gunther K., and Penzhorn R.D. J. Org. Chem. 38 (1973) 4070-4071
36. Caschili S., Delogu F., and Cao G. Annal. Chim. 95 (2005) 813-821