Oxidative cleavage of alkenes using an in situ generated iodonium ion with oxone as a terminal oxidant

Organic Letters

Volumn 12, Issue 24, 2010, Pages 5640-5643

  Thottumkara, Prem P ^a   Vinod, Thottumkara K ^a  

^a WESTERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650340898     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1023807     Document Type: Article

References (39)

1. Sheldon, R. A. and Kochi, J. K. Metal Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
2. Stewart, R. Oxidation in Organic Chemistry; Wiberg, K., Ed.; Academic Press: New York, 1965.
3. Hudlický, M. Oxidations in Organic Chemistry; American Chemical Society Monograph 186; American Chemical Society: Washington D.C., 1990.
4. Larock, R. C. Comprehensive Organic Transformations, 2 nd ed.; Wiley-VCH: New York, 1999; p 1234.
5. Lee, D. G. and Chen, T. Comprehensive Organic Synthesis; Trost, B. M. and Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 541.
6. Bailey, P. S. Ozonation In Organic Chemistry; Academic Press: New York, 1982.
7. Criegee, R. Angew. Chem., Int. Ed. Engl. 1975, 14, 745
8. Pappo, R.; Allen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478
9. Criegee, R.; Marchand, B.; Wannowius, H. Annalen 1942, 550, 99
10. Sharpless, K. B.; Teranishi, A. Y.; Backvall, J. E. J. Am. Chem. Soc. 1977, 99, 3120
11. Serious accidents due to explosions during ozonolysis have been reported. See
12. Koike, K.; Inoue, G.; Fukada, T. J. Chem. Eng. Jpn. 1999, 32, 295
13. Boer, J. W.; Brinksma, J.; Browne, W. R.; Meetsma, A.; Alsters, P. L.; Hage, R.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127, 7990
14. Biradar, A. V.; Sathe, B. R.; Umbarkar, S. B.; Dongare, M. K. J. Mol. Catal. A: Chem. 2008, 285, 111
15. Griffith, W. P.; Shoair, A. G.; Suriaatmaja, M. Synth. Commun. 2000, 30, 3091
16. Kogan, V.; Quintal, M. M.; Neumann, R. Org. Lett. 2005, 7, 5039
17. Plietker, B. J. Org. Chem. 2003, 68, 7123
18. Wang, A.; Jiang, H. J. Org. Chem. 2010, 75, 2321
19. Shing, T. K. M.; Tam, E. K. W. V.; Tai, W. -F.; Chung, I. H. F.; Jiang, Q. Chem. - Eur. J. 1996, 2, 50
20. Neisius, N. M.; Plietker, B. J. Org. Chem. 2008, 73, 3218
21. Travis, B. R.; Narayan, R. S.; Borhan, B. J. J. Am. Chem. Soc. 2002, 124, 3824
22. Kobayashi, S.; Endo, M.; Eagayama, S. J. Am. Chem. Soc. 1999, 121, 11229
23. Kobayashi, S.; Endo, M.; Nagayama, S. J. Org. Chem. 1998, 63, 6094
24. Ho, C. -M.; Yu, W. -Y.; Che, C. -M. Angew. Chem. Int. Ed 2004, 43, 3303
25. Miyamoto, K.; Tada, N.; Ochiai, M. J. Am. Chem. Soc. 2007, 129, 2772
26. Miyamoto, K.; Sei, Y.; Yamaguchi, K.; Ochiai, M. J. Am. Chem. Soc. 2009, 131, 1382
27. Van Rheeven, V.; Kelley, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 23, 1973
28. Nicolaou, K. C.; Adsool, V. A.; Hale, C. R. H. Org. Lett. 2010, 12, 1552
29. Thottumkara, A. P.; Bowsher, M. S.; Vinod, T. K. Org. Lett. 2005, 7, 2933
30. Ohja, L. R.; Kudugunti, S.; Maddukuri, P. P.; Kommareddy, A.; Gunna, M. R.; Dokuparthi, P.; Gottam, H. B.; Botha, K. K.; Parapati, D. R.; Vinod, T. K. SynLett 2009, 1, 117
31. Richter, H. W.; Cherry, B. R.; Zook, T. D.; Koser, G. F. J. Am. Chem. Soc. 1997, 119, 9614
32. Doan, L.; Bradley, K.; Gerdes, S.; Whalen, D. L. J. Org. Chem. 1999, 64, 6227
33. Travis, B. R.; Sivakumar, M.; Hollist, G. O.; Borhan, B. Org. Lett. 2003, 5, 1031
34. Gandhari, R.; Maddukuri, P. P.; Vinod, T. K. J. Chem. Educ. 2007, 84, 852
35. Oxone required for quantitative cleavage of susbtrates depend on the nature of the substrates employed and whether the initially formed cleaved products are further oxidized.
36. Yan, J.; Travis, B. R.; Borhan, B. J. Org. Chem. 2004, 69, 9299
37. Trost, B. M.; Curran, P. P. Tetrahedron Lett. 1981, 22, 1287
38. Full competition experiment data is provided in the Supporting Information.
39. 1H NMR sample with terephthalic acid increases the intensity of the singlet at 8.12; however, formation of terephthalic acid in the reaction medium is still being debated.