(Nitrosonaphtholato)metal complex-catalyzed oxidation of phenols and alkenes

Abstract

Bis(1-nitroso-2-naphtholato)manganese(II), tris(1-nitroso-2-naphtholato)manganese(III), tris(2-nitroso-1-naphtholato)manganese(III), bis(1-nitroso-2-naphtholato)cobalt(II), bis(1-nitroso-2-naphtholato)nickel(II), bis(1-nitroso-2-naphtholato)copper(II) and bis(1-nitroso-2-naphtholato)zinc(II) were prepared and their catalytic abilities in the oxidation of phenols were examined. The best yields of diphenoquinones were obtained when the catalytic oxidation using bis(1-nitroso-2-naphtholato)manganese(II) was carried out at 23 °C under an oxygen atmosphere (1 atm) in the presence of a phosphine ligand. Likewise, phenols were completely converted to the corresponding diphenoquinones together with small amounts of benzoquinones under an oxygen pressure (20 atm) at 50 °C in a short period of time. It was proven that the manganese(II) catalyst, molecular oxygen, and phosphine ligand were essential for the catalytic phenol oxidation. On the other hand, bis(1-nitroso-2-naphtholato)manganese(II)-catalyzed epoxidation of alkenes was only effective when iodosylbenzene was used. The catalytic oxidation mechanism was discussed on the basis of the measurement of cyclic voltammograms of the (nitrosonaphtholato)metal complexes, isolated intermediates, and effect of additives.

References

1. G. Balavoine, D. H. R. Barton, Y. V. Geletii and D. R. Hill, in The Activation of Dioxygen and Homogeneous Catalytic Oxidation, eds. D. H. R. Barton, A. E. Martell and D. T. Sawyer, Plenum Press, New York, 1993, p. 225.
2. (a) Cytochrome P-450, eds. R. Sato and T. Omura, Academic Press, New York, 1987; (b) T. J. McMurry and J. T. Groves, Cytochrome P-450: Structure, Mechanism, and Biochemistry, ed. P. Ortiz de Montellano, Chapter I, Plenum Press, New York, 1986; (c) J. P. Collman and S. E. Groh, J. Am. Chem. Soc., 1982, 104, 1391; (d) I. Tabushi and K. Morimitsu, J. Am. Chem. Soc., 1984, 106, 6871; (e) D. Mansury, Pure Appl. Chem., 1987, 59, 759.
3. (a) R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981; (b) P. A. Chaloner, Handbook of Coordination Catalysis in Organic Chemistry, Butterworths, London, 1986; (c) K. A. Jørgensen, Chem. Rev., 1989, 89, 431; (d) G. W. Parshall and S. D. Ittel, Homogeneous Catalysis, 2nd edn., Wiley, New York, 1992.
4. (a) S. Gurrieri and G. Siracusa, Inorg. Chim. Acta, 1971, 650 and references cited therein; (b) G. T. Morgan and J. D. M. Smith, J. Chem. Soc., 1921, 119, 704; (c) P. E. Wenger, D. Monnier and F. Jaccard, Helv. Chim. Acta, 1950, 33, 1458; (d) C. M. Callahan, W. C. Fernelius and B. P. Block, Anal. Chim. Acta, 1957, 16, 101; (e) K. B. Yatsimirskii and B. D. Berezin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1958, 6, 28; (f) E. K. Astakhova, V. M. Savostina and V. M. Peshkova, Vestn. Mosk. Univ., Khim., 1964, 19, 62; (g) J. Charalambous, M. J. Frazer and F. B. Taylor, J. Chem. Soc., 1969, 2787; (h) K. K. Chatterjee, Anal. Chim. Acta, 1959, 20, 423; (i) R. C. Aggarwal, R. Bala and R. L. Prasad, Synth. React. Inorg. Metal-Org. Chem., 1984, 14, 171; (j) D. Ray and A. Chakravorty, Inorg. Chem., 1988, 27, 3292.
5. D. Baluch, J. Charalambous, L. Lan and B. Haines, J. Chem. Soc., Chem. Commun., 1988, 1178.
6. (a) H. Nishino, N. Itoh, M. Nagashima and K. Kurosawa, Bull. Chem. Soc. Jpn., 1992, 65, 620; (b) K. Omura, J. Org. Chem., 1998, 63, 10031.
7. (a) T. Matsushita, H. Kono and T. Shono, Bull. Chem. Soc. Jpn., 1981, 54, 2646; (b) T. Matsushita, M. Fujiwara and T. Shono, Chem. Lett., 1981, 631; (c) T. Matsushita, Y. Hirata and T. Shono, Bull. Chem. Soc. Jpn., 1982, 55, 108.
8. (a) H. Hope, M. M. Olmstead, B. D. Murray and P. P. Power, J. Am. Chem. Soc., 1985, 107, 712; (b) I. R. Little and B. P. Straughan, J. Chem. Soc., Dalton Trans., 1986, 2211.
9. (a) T.-L. Ho, Hard and Soft Acids and Bases Principle in Organic Chemistry, Academic Press, New York, 1977; (b) J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, California, 1987.
10. E. G. Samsel, K. Srinivasan and J. K. Kochi, J. Am. Chem. Soc., 1985, 107, 7606.
11. (a) C. Walling and S. Kato, J. Am. Chem. Soc., 1971, 93, 4275; C. Walling, G. M. El-Taliawi and R. A. Johnson, J. Am. Chem. Soc., 1974, 96, 133; (b) A. Zombeck, R. S. Drago, B. B. Corden and J. H. Gaul, J. Am. Chem. Soc., 1981, 103, 7580; (c) S. A. Bedell and A. E. Martell, Inorg. Chem., 1983, 22, 364; X.-Y. Wang, R. J. Motekaitis and A. E. Martell, Inorg. Chem., 1984, 23, 271.
12. (a) K. Srinivasan, P. Michaud and J. K. Kochi, J. Am. Chem. Soc., 1986, 108, 2309; (b) T. Katsuki, J. Synth. Org. Chem. Jpn., 1995, 53, 940; Y. N. Ito and T. Katsuki, Tetrahedron Lett., 1998, 39, 4325.
13. L. F. Lindoy, V. Katovic and D. H. Busch, J. Chem. Educ., 1972, 49, 117.
14. A. Earnshaw, Introduction to Magnetochemistry, Academic Press, New York, 1968.
15. M. N. Bhattacharjee, M. K. Chaudhuri and D. T. Khathing, J. Chem. Soc., Dalton Trans., 1982, 669.
16. H. Nishino, Bull. Chem. Soc. Jpn., 1985, 58, 217.
17. H. Saltzman and J. G. Sharefkin, Org. Synth., Coll. Vol. 5, Wiley, New York, 1973, p. 658.
18. C. S. Marvel and P. K. Porter, Org. Synth., Coll. Vol. 1, Wiley, New York, 1967, p. 411.
19. V. Balogh, M. Fetizon and M. Goler, J. Org. Chem., 1971, 36, 1339.
20. J. H. Fookes, E. L. Pelton and M. W. Long Jr., USP 2, 885, 444/1959 (Chem. Abstr., 1960, 54, 5579i).
21. (a) J. Read and I. G. M. Campbell, J. Chem. Soc., 1930, 2377; (b) L. F. Lane and D. R. Walters, J. Am. Chem. Soc., 1951, 73, 4234.