Selective oxidation of olefins within organic dye cation-exchanged zeolites

Journal of the American Chemical Society

Volumn 118, Issue 43, 1996, Pages 10666-10667

  Li, Xiaoyuan ^a   Ramamurthy, V ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYE; PEROXIDE;

ARTICLE; OXIDATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0029837634     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9623727     Document Type: Article

References (47)

1. (a) Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979.
2. (b) Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vols. 1-4.
3. For a few selected reviews, see: (a) Foote, C. S. Acc. Chem. Res. 1968, 1, 104. (b) Keams, D. R. Chem. Rev. 1971, 71, 395. (c) Adam, W.; Prein, M. Acc. Chem. Res. 1996, 29, 275.
4. For a few selected reviews, see: (a) Foote, C. S. Acc. Chem. Res. 1968, 1, 104. (b) Keams, D. R. Chem. Rev. 1971, 71, 395. (c) Adam, W.; Prein, M. Acc. Chem. Res. 1996, 29, 275.
5. For a few selected reviews, see: (a) Foote, C. S. Acc. Chem. Res. 1968, 1, 104. (b) Keams, D. R. Chem. Rev. 1971, 71, 395. (c) Adam, W.; Prein, M. Acc. Chem. Res. 1996, 29, 275.
6. Recently, elegant examples of oxidation upon visible excitation of olefin-oxygen complex in zeolite has been reported by Frei and coworkers: (a) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1993, 115, 7501. (b) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 1812. (c) Sun, H.; Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 7951. (d) Blatter, F.; Moreau, F.; Frei, H. J. Phys. Chem. 1994, 98, 13403. (e) Blatter, F.; Sun, H.; Frei, H. Catal. Lett. 1995, 35, 1. (f) Blatter, F.; Sun, H.; Frei, H. Chem. Eur. J. 1996, 2, 113.
7. Recently, elegant examples of oxidation upon visible excitation of olefin-oxygen complex in zeolite has been reported by Frei and coworkers: (a) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1993, 115, 7501. (b) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 1812. (c) Sun, H.; Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 7951. (d) Blatter, F.; Moreau, F.; Frei, H. J. Phys. Chem. 1994, 98, 13403. (e) Blatter, F.; Sun, H.; Frei, H. Catal. Lett. 1995, 35, 1. (f) Blatter, F.; Sun, H.; Frei, H. Chem. Eur. J. 1996, 2, 113.
8. Recently, elegant examples of oxidation upon visible excitation of olefin-oxygen complex in zeolite has been reported by Frei and coworkers: (a) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1993, 115, 7501. (b) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 1812. (c) Sun, H.; Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 7951. (d) Blatter, F.; Moreau, F.; Frei, H. J. Phys. Chem. 1994, 98, 13403. (e) Blatter, F.; Sun, H.; Frei, H. Catal. Lett. 1995, 35, 1. (f) Blatter, F.; Sun, H.; Frei, H. Chem. Eur. J. 1996, 2, 113.
9. Recently, elegant examples of oxidation upon visible excitation of olefin-oxygen complex in zeolite has been reported by Frei and coworkers: (a) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1993, 115, 7501. (b) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 1812. (c) Sun, H.; Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 7951. (d) Blatter, F.; Moreau, F.; Frei, H. J. Phys. Chem. 1994, 98, 13403. (e) Blatter, F.; Sun, H.; Frei, H. Catal. Lett. 1995, 35, 1. (f) Blatter, F.; Sun, H.; Frei, H. Chem. Eur. J. 1996, 2, 113.
10. Recently, elegant examples of oxidation upon visible excitation of olefin-oxygen complex in zeolite has been reported by Frei and coworkers: (a) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1993, 115, 7501. (b) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 1812. (c) Sun, H.; Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 7951. (d) Blatter, F.; Moreau, F.; Frei, H. J. Phys. Chem. 1994, 98, 13403. (e) Blatter, F.; Sun, H.; Frei, H. Catal. Lett. 1995, 35, 1. (f) Blatter, F.; Sun, H.; Frei, H. Chem. Eur. J. 1996, 2, 113.
11. Recently, elegant examples of oxidation upon visible excitation of olefin-oxygen complex in zeolite has been reported by Frei and coworkers: (a) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1993, 115, 7501. (b) Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 1812. (c) Sun, H.; Blatter, F.; Frei, H. J. Am. Chem. Soc. 1994, 116, 7951. (d) Blatter, F.; Moreau, F.; Frei, H. J. Phys. Chem. 1994, 98, 13403. (e) Blatter, F.; Sun, H.; Frei, H. Catal. Lett. 1995, 35, 1. (f) Blatter, F.; Sun, H.; Frei, H. Chem. Eur. J. 1996, 2, 113.
12. (a) Ramamurthy, V.; Eaton, D. F.; Sanderson, D. R. J. Am. Chem. Soc. 1993, 115, 10438.
13. (b) Calzaferri, L. G.; Gfeller, N. J. Phys. Chem. 1992, 96, 3428.
14. (c) Wohrle, D.; Schulz-Ekloff, G. Adv. Mater. 1994, 6, 875.
15. Weiss, R. G.; Ramamurthy, V.; Hammond, G. S. Acc. Chem. Res. 1993, 26, 530.
16. (a) Breck, D. W. Zeolite Molecular Sieves: Structure, Chemistry and Use; John Wiley and Sons: New York, 1974.
17. (b) Dyer, A. An Introduction to Zeolite Molecular Sieves; John Wiley and Sons: New York, 1988.
18. (c) van Bekkum, H.; Flanigen, E. M.; Jansen, J. C. Introduction to Zeolite Science and Practice; Elsevier: Amsterdam, 1991.
19. Kasha, M.; Brabham, D. E. In Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979; p 1.
20. Excitation (>450 nm) of olefins 1-5 in Na Y in the absence of the dye did not give any products.
21. (a) Foote, C. S.; Wexler, S.; Ando, W.; Higgins, R. J. Am. Chem. Soc. 1968, 90, 975.
22. (b) Foote, C. S.; Denny, R. W. J. Am. Chem. Soc. 1971, 93, 5168.
23. (c) Foote, C. S. Pure Appl. Chem. 1971, 27, 635.
24. 9,10-Dicyanoanthracene (DCA) has been established to act both as an electron transfer and energy transfer sensitizer during the oxidation of olefins: (a) Foote, C. S. Tetrahedron 1985, 41, 2221. (b) Kanner, R. C.; Foote, C. S. J. Am. Chem. Soc. 1992, 114, 678, 682. (c) Arakai, Y.; Dobrowolski, D. C.; Goyne, T. E.; Hanson, D. C.; Jiang, Z. Q.; Lee, K. L.; Foote, C. S. J. Am. Chem. Soc. 1984, 106, 4570.
25. 9,10-Dicyanoanthracene (DCA) has been established to act both as an electron transfer and energy transfer sensitizer during the oxidation of olefins: (a) Foote, C. S. Tetrahedron 1985, 41, 2221. (b) Kanner, R. C.; Foote, C. S. J. Am. Chem. Soc. 1992, 114, 678, 682. (c) Arakai, Y.; Dobrowolski, D. C.; Goyne, T. E.; Hanson, D. C.; Jiang, Z. Q.; Lee, K. L.; Foote, C. S. J. Am. Chem. Soc. 1984, 106, 4570.
26. 9,10-Dicyanoanthracene (DCA) has been established to act both as an electron transfer and energy transfer sensitizer during the oxidation of olefins: (a) Foote, C. S. Tetrahedron 1985, 41, 2221. (b) Kanner, R. C.; Foote, C. S. J. Am. Chem. Soc. 1992, 114, 678, 682. (c) Arakai, Y.; Dobrowolski, D. C.; Goyne, T. E.; Hanson, D. C.; Jiang, Z. Q.; Lee, K. L.; Foote, C. S. J. Am. Chem. Soc. 1984, 106, 4570.
27. A few of the olefins investigated here have been established to quench the excited singlet of DCA by an electron transfer process (ref 9c).
28. (a) Keizer, P. N.; Morton, J. R.; Preston, K. F.; Sugden, J. J. Phys. Chem. 1991, 95, 7117.
29. (b) Gugel, A.; Mullen, K.; Reichert, H.; Schmidt, W.; Schon, G.; Schuth, F.; Spickermann, J.; Titman, J.; Unger, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 556. Anderson, M. W.; Shi, J.; Leigh, D. A.; Moody, A. E.; Wade, F. A.; Hamilton, B.; Carr, S. W. J. Chem. Soc., Chem. Commun. 1993, 533.
30. (b) Gugel, A.; Mullen, K.; Reichert, H.; Schmidt, W.; Schon, G.; Schuth, F.; Spickermann, J.; Titman, J.; Unger, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 556. Anderson, M. W.; Shi, J.; Leigh, D. A.; Moody, A. E.; Wade, F. A.; Hamilton, B.; Carr, S. W. J. Chem. Soc., Chem. Commun. 1993, 533.
31. Foote, C. S. Top. Curr. Chem. 1994, 109, 347.
32. 60/Na Y.
33. 60 plugged all entrances to the zeolite, the oxidation occurred in hexane solution.
34. (a) Gollnik, K. Adv. Chem. 1968, 77, 79.
35. (b) Stephenson, L. M.; Grdina, M. J.; Orfanopoulos, M. Acc. Chem. Res. 1980, 13, 419.
36. (c) Schulte-Elte, K. H.; Rautenstrauch, V. J. Am. Chem. Soc. 1980, 702, 1738.
37. (d) Hurst, J. R.; Schuster, G. J. Am. Chem. Soc. 1982, 104, 6854.
38. (e) Frimer, A.; Stephenson, L. M. In Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. 2, p 67.
39. (f) Gollnick, K.; Kuhn, H. J. In Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979; p 287.
40. (a) Schade, C.; Schleyer, P. v. R. Adv. Organomet. Chem. 1987, 27, 169.
41. (b) Setzer, W.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353.
42. (c) Staley, R. H.; Beauchamp, J. L. J. Am. Chem. Soc. 1975, 97, 5920.
43. (d) Sunner, J.; Nishizawa, K.; Kebarle, P. J. Phys. Chem. 1981, 85, 1814.
44. (e) Hepp, M. A.; Ramamurthy, V.; Corbin, D. R.; Dybowski, C. J. Phys. Chem. 1992, 96, 2629.
45. Independent of the cation, most of the olefin remained within the zeolite. However, in no case were all olefin molecules adsorbed within the zeolite. Also, at the end of the reaction no product remained in hexane portion.
46. (a) Leibovitch, M.; Olovsson, G.; Sundarababu, G.; Ramamurthy, V.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1996, 118, 1219.
47. (b) Sundarababu, G.; Leibovitch, M.; Corbin, D. R.; Scheffer, J. R.; Ramamurthy, V. J. Chem. Soc., Chem Commm. 1996, 2049.