First exclusive regioselective fragmentation of primary ozonides controlled by remote carbonyl groups and a new method for determining the regiochemistry of carbonyl oxide formation

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3820-3828

  Wu, Hsien Jen ^a   Lin, Chu Chung ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000379261     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952284p     Document Type: Article

References (31)

1. (a) Criegee, R.; Wenner, G. Ann. 1949, 564, 9.
2. (b) Criegee, R. Ann. 1953, 583, 1.
3. (c) Criegee, R. Angew. Chem., Int. Ed. Engl. 1975, 11, 745.
4. (a) Bailey, P. S. Ozonation in Organic Chemistry; Academic Press: New York, 1978, Vol. 1; 1982, Vol. 2.
5. (b) Bunnelle, W. H. Chem. Rev. 1991, 91, 335.
6. (c) McCullough, K. J.; Nojima, M. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992.
7. (d) Sander, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 344.
8. (a) Fliszar, S.; Renard, J.; Simon, D. Z. J. Am. Chem. Soc. 1971, 93, 6953.
9. (b) Griesbaum, K.; Greunig, H. J.; Volpp, W.; Jung, I. C. Chem. Ber. 1991, 124, 947.
10. (c) Griesbaum, K.; Zwick, G. Chem. Ber. 1986, 119, 229.
11. (d) Griesbaum, K.; Zwick, G.; Agarwal, S.; Keul, H.; Pfeffer, B.; Murray, R. W. J. Org. Chem. 1985, 50, 4194.
12. (e) Wojciechowski, B. J.; Chiang, C. Y.; Kuczkowski, R. L. J. Org. Chem. 1990, 55, 1120.
13. (a) Griesbaum, K.; Kiesel, G. Chem. Ber. 1989, 122, 145.
14. (b) Paryzek, Z.; Martynow, J.; Swoboda, W. J. Chem. Soc., Perkin Trans. 1 1990, 1222.
15. (c) Bunnelle, W. H.; Isbell, T. A. J. Org. Chem. 1992, 57, 729.
16. (c) Teshima, K.; Kawamura, S. I.; Ushigoe, Y.; Nojima, M.; McCullough, K. J. J. Org. Chem. 1995, 60, 4755.
17. (a) Williams, P. D.; LeGoff, E. J. Org. Chem. 1981, 46, 4143.
18. (b) Williams, P. D.; LeGoff, E. Tetrahedron Lett. 1985, 26, 1367.
19. (a) Ramanathan, V.; Levine, R. J. Org. Chem. 1962, 27, 1216.
20. (b) Gschwend, H. W.; Rodriguez, H. R. Org. React. 1979, 26, 31.
21. (a) Bailey, P. S.; Ferrell, T. M. J. Am. Chem. Soc. 1978, 100, 899.
22. (b) Lattimer, R. P.; Kuczkowski, R. L.; Gillies, C. L. J. Am. Chem. Soc. 1974, 96, 348.
23. (c) Kuczkowski, R. L. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; pp 197-276.
24. (d) Cremer, D. J. Am. Chem. Soc. 1981, 103, 3619.
25. (a) Razumovskii, S. D.; Zaikov, G. E. Ozone and its Reaction with Organic Compounds; Elsevier: The Netherlands, 1984; Chapter 9, p 370.
26. (b) Pobedimskii, D. G.; Razumovskii, S. D. Izv. Akad. Nauk SSSR, Ser. Khim 1970, 3, 602; Chem. Abstr. 1970, 73, 13853n.
27. (b) Pobedimskii, D. G.; Razumovskii, S. D. Izv. Akad. Nauk SSSR, Ser. Khim 1970, 3, 602; Chem. Abstr. 1970, 73, 13853n.
28. Hon, Y. S.; Yan, J. L. Tetrahedron Lett. 1993, 34, 6591.
29. (a) Wu, H. J.; Huang, F. J.; Lin, C. C. J. Chem. Soc., Chem. Commun. 1991, 770.
30. (b) Wu, H. J.; Lin, C. C.; Huang, F. J.; Lin, J. C. Submitted for publication.
31. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.