Activation of nitrous oxide and selective oxidation of alcohols and alkylarenes catalyzed by the [PV2MO10O40]5- polyoxometalate ion

Angewandte Chemie - International Edition

Volumn 42, Issue 1, 2003, Pages 92-95

  Ben Daniel, Revital ^a   Neumann, Ronny ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

Alcohols; Homogeneous catalysis; Nitrogen oxides; Oxidation; Polyoxometalates

Indexed keywords

ALDEHYDES; CATALYSTS; CHEMICAL ACTIVATION; KETONES; NITROGEN OXIDES; OXIDATION;

CATALYTIC OXIDATION;

ALCOHOLS;

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKYL GROUP; AROMATIC COMPOUND; KETONE DERIVATIVE; METAL DERIVATIVE; MOLYBDIC ACID; NITROUS OXIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYOXOMETALATE; UNCLASSIFIED DRUG; VANADIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; OXIDATION; REACTION ANALYSIS; REDUCTION;

EID: 0037414949     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390062     Document Type: Article

References (32)

1. R. G. S. Banks, R. J. Henderson, J. M. Pratt, J. Chem. Soc. A 1968, 2886-2889.
2. F. Bottomley, I. J. B. Lin, M. Mukaida, J. Am. Chem. Soc, 1980, 102, 5238-5342.
3. K. J. Zhen, M. M. Khan, C. H. Mak, K. B. Lewis, G. A. Somorjai, J. Catal. 1985, 94, 501-507; H. F. Liu, R. S. Liu, K. Y. Liew, R. E. Johnson, J. H. Lunsford, J. Am. Chem. Soc. 1984, 106, 4117-4121.
4. K. J. Zhen, M. M. Khan, C. H. Mak, K. B. Lewis, G. A. Somorjai, J. Catal. 1985, 94, 501-507; H. F. Liu, R. S. Liu, K. Y. Liew, R. E. Johnson, J. H. Lunsford, J. Am. Chem. Soc. 1984, 106, 4117-4121.
5. G. I. Panov, CATTECH 2000, 4, 18-32; G. I. Panov, A. Uriate, M. A. Rodkin, V. I. Sobolev, Catal. Today 1998, 41, 365-385.
6. G. I. Panov, CATTECH 2000, 4, 18-32; G. I. Panov, A. Uriate, M. A. Rodkin, V. I. Sobolev, Catal. Today 1998, 41, 365-385.
7. N. P. Notte, Top. Catal. 2000, 13, 387-394.
8. M. A. Rhodkin, V. I. Sobolev, K. A. Dubkov, N. H. Watkins, G. I. Panov, Stud. Surf. Sci. Catal. 2000, 130A, 881-886.
9. P. Mansunaga, G. L. Hillhouse, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 2075-2077; G. A. Vaughan, D. Chadwick, G. L. Hillhouse, A. L. Rheingold, J. Am. Chem. Soc. 1989, 111, 5491-5493; A. M. Baranger, T. A. Hanna, R. G. Bergman, J. Am. Chem. Soc. 1995, 117, 10041-10046.
10. P. Mansunaga, G. L. Hillhouse, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 2075-2077; G. A. Vaughan, D. Chadwick, G. L. Hillhouse, A. L. Rheingold, J. Am. Chem. Soc. 1989, 111, 5491-5493; A. M. Baranger, T. A. Hanna, R. G. Bergman, J. Am. Chem. Soc. 1995, 117, 10041-10046.
11. P. Mansunaga, G. L. Hillhouse, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 2075-2077; G. A. Vaughan, D. Chadwick, G. L. Hillhouse, A. L. Rheingold, J. Am. Chem. Soc. 1989, 111, 5491-5493; A. M. Baranger, T. A. Hanna, R. G. Bergman, J. Am. Chem. Soc. 1995, 117, 10041-10046.
12. A. R. Johnson, W. M. Davis, C. C. Cummins, S. Serron, S. P. Nolan, D. J. Masaev, K. Morokuma, J. Am. Chem. Soc. 1998, 120, 2071-2085; C. E. Laplaza, A. L. Odom, W. M. Davis, C. C. Cummins, J. D. Protasiewicz, J. Am. Chem. Soc. 1995, 117, 4999-5000.
13. A. R. Johnson, W. M. Davis, C. C. Cummins, S. Serron, S. P. Nolan, D. J. Masaev, K. Morokuma, J. Am. Chem. Soc. 1998, 120, 2071-2085; C. E. Laplaza, A. L. Odom, W. M. Davis, C. C. Cummins, J. D. Protasiewicz, J. Am. Chem. Soc. 1995, 117, 4999-5000.
14. C. B. Pamplin, E. S. F. Ma, N. Safari, S. J. Rettig, B. R. James, J. Am. Chem. Soc 2001, 123, 8596-8597.
15. R. R. Conry, J. M. Mayer, Inorg. Chem. 1990, 29, 4862-4867; W. A. Howard, G. Parkin, J. Am. Chem. Soc. 1994, 116, 606-615.
16. R. R. Conry, J. M. Mayer, Inorg. Chem. 1990, 29, 4862-4867; W. A. Howard, G. Parkin, J. Am. Chem. Soc. 1994, 116, 606-615.
17. J. T. Groves, J. S. Roman, J. Am. Chem. Soc. 1995, 117, 5594-5595.
18. T. Yamada, K. Hashimoto, Y. Kitaichi, K. Suzuki, T. Ikeno, Chem. Lett. 2001, 268-269.
19. K. Hashimoto, Y. Kitaichi, H. Tanaka, T. Ikeno, T. Yamada, Chem. Lett. 2001, 922-923.
20. N. Mizuno, M. Misono, Chem. Rev. 1998, 98, 171-199; C. L. Hill, C. M. Prosser-McCartha, Coord. Chem. Rev. 1995, 143, 407-455; I. V. Kozhevnikov, Chem. Rev. 1998, 98, 171-198; R. Neumann, Prog. Inorg. Chem. 1998, 47, 317-370.
21. N. Mizuno, M. Misono, Chem. Rev. 1998, 98, 171-199; C. L. Hill, C. M. Prosser-McCartha, Coord. Chem. Rev. 1995, 143, 407-455; I. V. Kozhevnikov, Chem. Rev. 1998, 98, 171-198; R. Neumann, Prog. Inorg. Chem. 1998, 47, 317-370.
22. N. Mizuno, M. Misono, Chem. Rev. 1998, 98, 171-199; C. L. Hill, C. M. Prosser-McCartha, Coord. Chem. Rev. 1995, 143, 407-455; I. V. Kozhevnikov, Chem. Rev. 1998, 98, 171-198; R. Neumann, Prog. Inorg. Chem. 1998, 47, 317-370.
23. N. Mizuno, M. Misono, Chem. Rev. 1998, 98, 171-199; C. L. Hill, C. M. Prosser-McCartha, Coord. Chem. Rev. 1995, 143, 407-455; I. V. Kozhevnikov, Chem. Rev. 1998, 98, 171-198; R. Neumann, Prog. Inorg. Chem. 1998, 47, 317-370.
24. R. Ben-Daniel, L. Weiner, R. Neumann, J. Am. Chem. Soc. 2002, 124, 8788-8789.
25. 2, but the reaction is rarely selective for aliphatic primary alcohols, see: R. A. Sheldon, Catal. Today 2000, 57, 157-166.
26. A. M. Khenkin, I. Vigdergauz, R. Neumann, Chem. Eur. J. 2000, 6, 875-882; R. Neumann, M. Levin, J. Org. Chem. 1991, 56, 5707-5710.
27. A. M. Khenkin, I. Vigdergauz, R. Neumann, Chem. Eur. J. 2000, 6, 875-882; R. Neumann, M. Levin, J. Org. Chem. 1991, 56, 5707-5710.
28. There is no exact correlation between the gas-phase ionization potential and the solution oxidation potential which is the more relevant, but unknown, parameter.
29. I. A. Weinstock, Chem. Rev. 1998, 98, 113-170; A. M. Khenkin, L. Weiner, Y. Wang, R. Neumann, J. Am. Chem. Soc. 2001, 123, 8531-8542.
30. I. A. Weinstock, Chem. Rev. 1998, 98, 113-170; A. M. Khenkin, L. Weiner, Y. Wang, R. Neumann, J. Am. Chem. Soc. 2001, 123, 8531-8542.
31. Benzylic C-H bond strengths are proportional to the benzylic C-H stretch vibration, as taken from the gas-phase IR spectra. IR data from NIST at http://webbook.nist.gov/chemistry.
32. 18O was not commercially available and is prohibitively expensive to synthesize.