A new catalytic system for the selective aerobic oxidation of large ring cycloalkanes to ketones

Organic Process Research and Development

Volumn 7, Issue 3, 2003, Pages 426-428

  Baucherel, Xavier ^a   Arends, Isabel W C E ^a   Ellwood, S ^b   Sheldon, Roger A ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b Givaudan SA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; CYCLOALKANE DERIVATIVE; KETONE DERIVATIVE; SACCHARIN DERIVATIVE;

ARTICLE; CATALYSIS; GAS CHROMATOGRAPHY; ISOMER; MASS SPECTROMETRY; OXIDATION; REACTION OPTIMIZATION;

EID: 0037708555     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0340199     Document Type: Article

References (15)

1. Sheldon, R. A.; Kochi, J. K. Metal-Catalysed Oxidations of Organic Compounds; Academic Press: New York, 1981. Hill, C. L. Activation and Functionalization of Alkanes; Academic Press: New York, 1989. Fisher, W. B.; Van Peppen, J. P. Kirk-Othmer Encyclopaedia of Chemical Technology, 4th ed.; Wiley: New York, 1996; Vol. 7, pp 851-859.
2. Sheldon, R. A.; Kochi, J. K. Metal-Catalysed Oxidations of Organic Compounds; Academic Press: New York, 1981. Hill, C. L. Activation and Functionalization of Alkanes; Academic Press: New York, 1989. Fisher, W. B.; Van Peppen, J. P. Kirk-Othmer Encyclopaedia of Chemical Technology, 4th ed.; Wiley: New York, 1996; Vol. 7, pp 851-859.
3. Sheldon, R. A.; Kochi, J. K. Metal-Catalysed Oxidations of Organic Compounds; Academic Press: New York, 1981. Hill, C. L. Activation and Functionalization of Alkanes; Academic Press: New York, 1989. Fisher, W. B.; Van Peppen, J. P. Kirk-Othmer Encyclopaedia of Chemical Technology, 4th ed.; Wiley: New York, 1996; Vol. 7, pp 851-859.
4. Rademacher, H. Ullmann's Encyclopedia Industrial Organic Chemical; Wiley-VCH: Weinheim, 1999; Vol. 3, pp 1783-1787.
5. Bashkirov, A. N.; Kamzolkin, V. V.; Sokova, K. M.; Andreyeva, T. P. Oxidation of Hydrocarbons in Liquid Phase; Pergamon: Oxford, 1965; p 183.
6. Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Takeno, M.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520-4526. Ishii, Y.; Sakaguchi, S. Catalysis Surveys from Japan 1999, 3, 27-35. Ishii, Y. T. Eur. Pat., EP 0 824 962 A1. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393-427.
7. Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Takeno, M.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520-4526. Ishii, Y.; Sakaguchi, S. Catalysis Surveys from Japan 1999, 3, 27-35. Ishii, Y. T. Eur. Pat., EP 0 824 962 A1. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393-427.
8. Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Takeno, M.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520-4526. Ishii, Y.; Sakaguchi, S. Catalysis Surveys from Japan 1999, 3, 27-35. Ishii, Y. T. Eur. Pat., EP 0 824 962 A1. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393-427.
9. Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Takeno, M.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520-4526. Ishii, Y.; Sakaguchi, S. Catalysis Surveys from Japan 1999, 3, 27-35. Ishii, Y. T. Eur. Pat., EP 0 824 962 A1. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393-427.
10. Wentzel, B. B.; Donners, M. P. J.; Alsters, P. L.; Feiters, M. C.; Nolte, R. J. M. Tetrahedron 2000, 56, 7797-7803.
11. Gorgy, K.; Lepretre, J.-C.; Saint-Aman, E.; Einhorn, C.; Einhorn, J.; Marcadal, C.; Pierre, J.-L. Electrochim. Acta 1998, 44, 385-393.
12. Nagasawa, H. T.; Kawle, S. P.; Elberling, J. A.; DeMaster, E. G.; Fukuto, J. M. J. Med. Chem. 1995, 38, 1865-1871.
13. Arends, I. W. C. E.; Sasidharan, M.; Kühnle, A.; Duda, M.; Jost, C.; Sheldon, R. A. Tetrahedron 2002, 58, 9055-9061.
14. Matsunaka, K.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1999, 40, 2165-2168.
15. 3 at 100°C with NHS (as in run 4, Table 2). In this case 12% of the added ketone was decomposed after 6 h into a variety of products. A similar procedure was used to test the alcohol stability under these conditions using a mixture of cyclopentadecanol and cyclododecane. It was demonstrated that the alcohol is converted for almost 85% to the ketone and 9% to the diacid.