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

Author:

Maranzana Andrea1,Ghigo Giovanni1,Tonachini Glauco1

Affiliation:

1. Contribution from the Dipartimento di Chimica Generale e Organica Applicata, Università di Torino, Corso Massimo D'Azeglio 48, 10125 Torino, Italy

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Reference84 articles.

1. Photochemistry

2. (c) Dussault, P. Reactions of Hydroperoxides and Peroxides.Ibid., Chapter 5, pp 176, 177.

3. Wayne, R. P.Chemistry of Atmospheres; Clarendon Press:  Oxford, U.K., 1996; p 86.

4. Plesnicar, B. Polyoxides. InOrganic Peroxides; Ando, W., Ed.; John Wiley and Sons:  New York, 1992; Chapter 10, pp 489−494. (b) Yamaguchi, K.; Takada, K.; Otsuji, Y.; Mizuno, K. Theoretical and General Aspects of Organic Peroxides.Ibid., Chapter 1, pp 65−68. (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.Tetrahedron1998,54, 6939−6946. Lopez, L.; Troisi L.Tetrahedron1992,48, 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. (d) Reference 4c, p 221.

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