Selectivity in Lewis acid-mediated fragmentations of peroxides and ozonides: Application to the synthesis of alkenes, homoallyl ethers, and 1,2-dioxolanes

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 17, 2000, Pages 3006-3013

  Dussault, Patrick H ^a   Lee, Hyung Jae ^a   Liu, Xuejun ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DECOMPOSITION; ETHERS; IONIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; SYNTHESIS (CHEMICAL);

FRAGMENTATION;

PEROXIDES;

EID: 77956650813     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001391i     Document Type: Article

References (30)

1. H. Kropf, in Methods in Organic Chemistry (Houben-Weyl) Organische Peroxo-Verbindungen, ed. H. Kropf, Georg Thieme Verlag, Stuttgart, 1988, p. 1084.
2. P. H. Dussault, in Active Oxygen in Chemistry, ed. C. S. Foote, J. S. Valentine, A. Greenberg and J. F. Liebman, Blackie A & P, London, 1995, p. 141.
3. A. J. Bloodworth, N. Hargreaves and J. C. Mitchell, J. Chem. Res. (S), 1986, 390.
4. K. J. McCullough and M. Nojima, in Organic Peroxides, ed. W. Ando, John Wiley & Sons, Chichester, 1992, p. 661.
5. H. W. Gardner and R. D. Plattner, Lipids, 1984, 19, 294.
6. Y.-M. Pu, H. Yeh and H. Ziffer, Heterocycles, 1993, 36, 2099.
7. R. M. Goodman and Y. Kishi, J. Org. Chem., 1994, 59, 5125.
8. P. H. Dussault, I. Q. Lee, H.-J. Lee, Q. J. Niu, J. A. Schultz and U. R. Zope, J. Org. Chem., 2000, 65, submitted.
9. R. Lee, Ph.D. Thesis, University of Nebraska-Lincoln, 1996.
10. P. H. Dussault and A. Sahli, J. Org. Chem., 1992, 57, 1009.
11. P. H. Dussault, S. Kreifels and I. Q. Lee, Synth. Commun., 1995, 25, 2613.
12. K. Griesbaum, X. Liu and Y. Dong, Tetrahedron, 1997, 53, 5463.
13. K. Griesbaum, Trends Org. Chem., 1997, 6, 145.
14. R. C. Corcoran, Tetrahedron Lett., 1990, 31, 2101.
15. H. Nishiyama and K. Itoh, J. Org. Chem., 1982, 47, 2496.
16. W. Adam, A. Griesbeck and E. Staab, Angew. Chem., Int. Ed. Engl., 1986, 25, 269.
17. G. E. Keck, D. E. Abbott, E. P. Boden and E. J. Enholm, Tetrahedron Lett., 1984, 24, 3927.
18. S. C. Vonwiller, J. A. Warren, S. T. Mann and R. K. Haynes, Tetrahedron Lett., 1997, 38, 2363.
19. P. H. Dussault and X. Liu, Tetrahedron Lett., 1999, 40, 6553.
20. M. Miura and M. Nojima, J. Chem. Soc., Chem. Commun., 1979, 467.
21. M. Miura, M. Nojima and S. Kusabayashi, J. Chem. Soc., Perkin Trans. 1, 1980, 2909.
22. M. Miura, S. Nagase, M. Nojima and S. Kusabayashi, J. Org. Chem., 1983, 48, 2366.
23. M. Miura, M. Yoshida, M. Nojima and S. Kusabayashi, J. Chem. Soc., Chem. Commun., 1982, 397.
24. P. H. Dussault, C. T. Eary, R. J. Lee and U. R. Zope, J. Chem. Soc., Perkin Trans. 1, 1999, 2189.
25. E. S. Shanley, in Organic Peroxides, ed. D. Swern, Wiley-Interscience, New York, 1970, vol. 3, p. 341.
26. P. Patnaik, A Comprehensive Guide to the Hazardous Properties of Chemical Substances, Van Nostrand Reinhold, New York, 1992, p. 763.
27. L. A. Medard, Accidental Explosions: Types of Explosive Substances, Ellis Horwood Limited, Chichester, 1989, vol. 2.
28. G. O. Schenck and K.-H. Schulte-Elte, Justus Liebigs Ann. Chem., 1958, 618, 185.
29. H.-S. Dang, A. G. Davies, I. G. E. Davison and C. H. Schiesser, J. Org. Chem., 1990, 55, 1432.
30. N. A. Porter, J. K. Kaplan and P. H. Dussault, J. Am. Chem. Soc., 1990, 112, 1266.