Diradical and peroxirane pathways in the [π2 + π2] cycloaddition reactions of 1Δg dioxygen with ethene, methyl vinyl ether, and butadiene: A density functional and multireference perturbation theory study

Journal of the American Chemical Society

Volumn 122, Issue 7, 2000, Pages 1414-1423

  Maranzana, Andrea ^a   Ghigo, Giovanni ^a   Tonachini, Glauco ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; ETHER DERIVATIVE; ETHYLENE; ETHYLENE OXIDE DERIVATIVE; OXYGEN; RADICAL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENERGY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033996913     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990805a     Document Type: Article

References (24)

1. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Science: Cambridge, MA, 1995; Chapter 11.
2. (a) Foote, C. S.; Clennan, E. L. Properties and Reactions of Singlet Dioxygen. In Active Oxygen in Chemistry; Foote, C. S., Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional (Chapmann & Hall): New York, 1995; Chapter 4.
3. (b) Atkinson, R. Reactions of Oxygen Species in the Atmosphere. Ibid., Chapter 7.
4. (c) Dussault, P. Reactions of Hydroperoxides and Peroxides. Ibid., Chapter 5, pp 176, 177.
5. (d) Bielski, B. H.; Cabelli, D. E. Superoxide and Hydroxyl Radical Chemistry in Aqueous Solution. Ibid., Chapter 7.
6. (e) See ref 2a, pp 107-109, 119, 120, and 132, for some recent studies.
7. Wayne, R. P. Chemistry of Atmospheres; Clarendon Press: Oxford, U.K., 1996; p 86.
8. Plesnicar, B. Polyoxides. In Organic Peroxides; Ando, W., Ed.; John Wiley and Sons: New York, 1992; Chapter 10, pp 489-494.
9. (b) Yamaguchi, K.; Takada, K.; Otsuji, Y.; Mizuno, K. Theoretical and General Aspects of Organic Peroxides. Ibid., Chapter 1, pp 65-68.
10. (c) The other one is the Kopecky method, a β-halo hydroperoxide cyclization. See: Adam, W.; Heil, M.; Mosland, T.; Saha-Möller, C. R. Dioxetanes and α-Peroxy Lactones, Ring Cyclic Peroxides. Ibid., Chapter 5, p 223 ff. For other synthetic methods, see for instance: Lopez, L.; Farinola, G. M.; Nacci, A.; Sportelli, S. Tetrahedron 1998, 54, 6939-6946. Lopez, L.; Troisi L. Tetrahedron 1992, 48, 7321-7330. Lopez, L.; Troisi, L. Gazz. Chim. Ital. 1992,122, 507-509. Lopez, L.; Troisi, L.; Mele, G. Tetrahedron Lett. 1991, 32, 117-120. Posner, G. H.; Webb, K. S.; Nelson, W. M.; Kishimoto, T.; Seliger, H. H. J. Org. Chem. 1989, 54, 3252-3254. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1988, 29, 3145-3148. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319-5322.
11. (c) The other one is the Kopecky method, a β-halo hydroperoxide cyclization. See: Adam, W.; Heil, M.; Mosland, T.; Saha-Möller, C. R. Dioxetanes and α-Peroxy Lactones, Ring Cyclic Peroxides. Ibid., Chapter 5, p 223 ff. For other synthetic methods, see for instance: Lopez, L.; Farinola, G. M.; Nacci, A.; Sportelli, S. Tetrahedron 1998, 54, 6939-6946. Lopez, L.; Troisi L. Tetrahedron 1992, 48, 7321-7330. Lopez, L.; Troisi, L. Gazz. Chim. Ital. 1992,122, 507-509. Lopez, L.; Troisi, L.; Mele, G. Tetrahedron Lett. 1991, 32, 117-120. Posner, G. H.; Webb, K. S.; Nelson, W. M.; Kishimoto, T.; Seliger, H. H. J. Org. Chem. 1989, 54, 3252-3254. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1988, 29, 3145-3148. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319-5322.
12. (c) The other one is the Kopecky method, a β-halo hydroperoxide cyclization. See: Adam, W.; Heil, M.; Mosland, T.; Saha-Möller, C. R. Dioxetanes and α-Peroxy Lactones, Ring Cyclic Peroxides. Ibid., Chapter 5, p 223 ff. For other synthetic methods, see for instance: Lopez, L.; Farinola, G. M.; Nacci, A.; Sportelli, S. Tetrahedron 1998, 54, 6939-6946. Lopez, L.; Troisi L. Tetrahedron 1992, 48, 7321-7330. Lopez, L.; Troisi, L. Gazz. Chim. Ital. 1992,122, 507-509. Lopez, L.; Troisi, L.; Mele, G. Tetrahedron Lett. 1991, 32, 117-120. Posner, G. H.; Webb, K. S.; Nelson, W. M.; Kishimoto, T.; Seliger, H. H. J. Org. Chem. 1989, 54, 3252-3254. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1988, 29, 3145-3148. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319-5322.
13. (c) The other one is the Kopecky method, a β-halo hydroperoxide cyclization. See: Adam, W.; Heil, M.; Mosland, T.; Saha-Möller, C. R. Dioxetanes and α-Peroxy Lactones, Ring Cyclic Peroxides. Ibid., Chapter 5, p 223 ff. For other synthetic methods, see for instance: Lopez, L.; Farinola, G. M.; Nacci, A.; Sportelli, S. Tetrahedron 1998, 54, 6939-6946. Lopez, L.; Troisi L. Tetrahedron 1992, 48, 7321-7330. Lopez, L.; Troisi, L. Gazz. Chim. Ital. 1992,122, 507-509. Lopez, L.; Troisi, L.; Mele, G. Tetrahedron Lett. 1991, 32, 117-120. Posner, G. H.; Webb, K. S.; Nelson, W. M.; Kishimoto, T.; Seliger, H. H. J. Org. Chem. 1989, 54, 3252-3254. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1988, 29, 3145-3148. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319-5322.
14. (c) The other one is the Kopecky method, a β-halo hydroperoxide cyclization. See: Adam, W.; Heil, M.; Mosland, T.; Saha-Möller, C. R. Dioxetanes and α-Peroxy Lactones, Ring Cyclic Peroxides. Ibid., Chapter 5, p 223 ff. For other synthetic methods, see for instance: Lopez, L.; Farinola, G. M.; Nacci, A.; Sportelli, S. Tetrahedron 1998, 54, 6939-6946. Lopez, L.; Troisi L. Tetrahedron 1992, 48, 7321-7330. Lopez, L.; Troisi, L. Gazz. Chim. Ital. 1992,122, 507-509. Lopez, L.; Troisi, L.; Mele, G. Tetrahedron Lett. 1991, 32, 117-120. Posner, G. H.; Webb, K. S.; Nelson, W. M.; Kishimoto, T.; Seliger, H. H. J. Org. Chem. 1989, 54, 3252-3254. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1988, 29, 3145-3148. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319-5322.
15. (c) The other one is the Kopecky method, a β-halo hydroperoxide cyclization. See: Adam, W.; Heil, M.; Mosland, T.; Saha-Möller, C. R. Dioxetanes and α-Peroxy Lactones, Ring Cyclic Peroxides. Ibid., Chapter 5, p 223 ff. For other synthetic methods, see for instance: Lopez, L.; Farinola, G. M.; Nacci, A.; Sportelli, S. Tetrahedron 1998, 54, 6939-6946. Lopez, L.; Troisi L. Tetrahedron 1992, 48, 7321-7330. Lopez, L.; Troisi, L. Gazz. Chim. Ital. 1992,122, 507-509. Lopez, L.; Troisi, L.; Mele, G. Tetrahedron Lett. 1991, 32, 117-120. Posner, G. H.; Webb, K. S.; Nelson, W. M.; Kishimoto, T.; Seliger, H. H. J. Org. Chem. 1989, 54, 3252-3254. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1988, 29, 3145-3148. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319-5322.
16. (c) The other one is the Kopecky method, a β-halo hydroperoxide cyclization. See: Adam, W.; Heil, M.; Mosland, T.; Saha-Möller, C. R. Dioxetanes and α-Peroxy Lactones, Ring Cyclic Peroxides. Ibid., Chapter 5, p 223 ff. For other synthetic methods, see for instance: Lopez, L.; Farinola, G. M.; Nacci, A.; Sportelli, S. Tetrahedron 1998, 54, 6939-6946. Lopez, L.; Troisi L. Tetrahedron 1992, 48, 7321-7330. Lopez, L.; Troisi, L. Gazz. Chim. Ital. 1992,122, 507-509. Lopez, L.; Troisi, L.; Mele, G. Tetrahedron Lett. 1991, 32, 117-120. Posner, G. H.; Webb, K. S.; Nelson, W. M.; Kishimoto, T.; Seliger, H. H. J. Org. Chem. 1989, 54, 3252-3254. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1988, 29, 3145-3148. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319-5322.
17. (c) The other one is the Kopecky method, a β-halo hydroperoxide cyclization. See: Adam, W.; Heil, M.; Mosland, T.; Saha-Möller, C. R. Dioxetanes and α-Peroxy Lactones, Ring Cyclic Peroxides. Ibid., Chapter 5, p 223 ff. For other synthetic methods, see for instance: Lopez, L.; Farinola, G. M.; Nacci, A.; Sportelli, S. Tetrahedron 1998, 54, 6939-6946. Lopez, L.; Troisi L. Tetrahedron 1992, 48, 7321-7330. Lopez, L.; Troisi, L. Gazz. Chim. Ital. 1992,122, 507-509. Lopez, L.; Troisi, L.; Mele, G. Tetrahedron Lett. 1991, 32, 117-120. Posner, G. H.; Webb, K. S.; Nelson, W. M.; Kishimoto, T.; Seliger, H. H. J. Org. Chem. 1989, 54, 3252-3254. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1988, 29, 3145-3148. Curci, R.; Lopez, L.; Troisi, L.; Rashid, S. M. K.; Schaap, A. P. Tetrahedron Lett. 1987, 28, 5319-5322.
18. (d) Reference 4c, p 221.
19. (a) Marusak, R. A.; Meares, C. F. Metal-Complex Catalyzed Cleavage of Biopolymers. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional (Chapmann & Hall): New York, 1995; Chapter 8.
20. (b) Halliwell, B. The Biological Significance of Oxygen-Derived Species. Ibid., Chapter 7.
21. (c) Greenberg, A. Exploration of Selected Pathways for Metabolic Oxidative Ring Opening of Benzene Based on Estimates of Molecular Energetics. Ibid., Chapter 9, pp 415-419.
22. March, J. Advanced Organic Chemistry, 4th ed.; J. Wiley & Sons: New York, 1992; Chapter 5, Section 37.
23. Jefford, C. W. Chem. Soc. Rev. 1993, 59-66.
24. Frimer, A. A. Chem. Rev. 1979, 79, 359-387.