Iron(III )–Ethylenediaminetetraacetic AcidMediated Oxidation of Thiols to Disulfides with MolecularOxygen†

Abstract

Fe^III –EDTA in aqueous methanoloffers a simple environmentally acceptable synthetic tool foroxidizing thiols to the corresponding disulfides by molecularoxygen in excellent yields, under mild conditions and devoid ofside reactions.

References

1. C. Lopez, A. Gonzalez, F. P. Cossio and C. Palomo, Synth. Commun., 1985, 15, 1197.
2. E. Santaniello, F. Milani and R. Casati, Synthesis, 1983, 749.
3. E. P. Papadopoulos, A. Jarrar and C. H. Issidorides, J. Org. Chem., 1966, 31, 615.
4. F. Yoneda, K. Suzuki and Y. Nitta, J. Org. Chem., 1967, 32, 727.
5. J. M. Aizpurua, M. Juaristi, B. Lecea and C. Palomo, Tetrahedron, 1985, 41, 2903.
6. K. Nakagawa, S. Shiba, M. Horikawa, K. Sato, H. Nakamura, N. Harada and F. Harada, Synth. Commun., 1980, 10, 305.
7. H. Firouzabadi, N. Iranpoor, F. Kiaeezadeh and J. Toofan, Tetrahedron, 1986, 42, 719.
8. S. V. Ley, C. A. Meerholz and D. H. R. Barton, Tetrahedron, Suppl., 1981, 213.
9. H. A. Muathen, Indian J. Chem., 1991, 30B, 522.
10. A. McKillop, D. Koyuncu, A. Krief, W. Dumont, P. Renier and M. Trabelsi, Tetrahedron Lett., 1990, 31, 5007.
11. H. Tamamura, A. Otaka, J. Nakamura, K. Okubo, T. Koide, K. Ikeda and N. Fujii, Tetrahedron Lett., 1993, 34, 4931.
12. L. I. Simandi, Catalytic Activation of Dioxygen by Metal Complexes, Kluwer, Boston, 1992; The Activation of Dioxygen and Homogeneous Catalytic Oxidation, ed. D. H. R. Barton, A. E. Martel and D. T. Sawyer, Plenum Press, New York, 1993.
13. S. Basu, S. Satapathy and A. K. Bhatnagar, Catal. Rev.-Sci. Eng., 1993, 35, 571.
14. K.-T. Liu and Y.-C. Tong, Synthesis, 1978, 669.
15. A. K. Yatsimirskii, E. I. Kozlyak and A. S. Erokhin, Kinet. Catal., 1988, 29, 305.
16. A. Cervilla, A. Corma, V. Fornes, E. Lopis, P. Palanca, F. Rey and A. Ribera, J. Am. Chem. Soc., 1994, 116, 1595.
17. L. I. Simandi, S. Nemeth and N. Rumelis, J. Mol. Catal., 1987, 42, 357.
18. S. Uemura, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, New York, 1991, vol. 7, pp. 757–787.
19. W. A. Knepper, in Kirk-Othmer Encyclopedia of Chemical Technology, Wiley, New York, 3rd edn., 1981, vol. 13, pp. 735–753.
20. D. Lionel and P. Laszlo, J. Org. Chem., 1996, 61, 6360.
21. B. Sain, P. S. Murthy, T. Venkateshwar Rao, T. S. R. Prasada Rao and G. C. Joshi, Tetrahedron Lett., 1994, 35, 5083.
22. J. R. Hart, Chemtech., 1987, 17, 313.
23. C. F. Cullis, J. D. Hopton, C. J. Swan and D. L. Trimm, J. Appl. Chem., 1968, 18, 335.
24. H. J. Wubs and A. A. C. M. Beenackers, AIChE J., 1994, 40, 433.
25. G. A. Olah, M. Arvanaghi and Y. D. Vankar, Synthesis, 1979, 721.
26. E. Miller, F. S. Crossley and M. L. Moore, J. Am. Chem. Soc., 1942, 64, 2322.
27. H. E. Westlake Jr and G. Dougherty, J. Am. Chem. Soc., 1942, 64, 149.