Benzeneseleninic anhydride oxidation of 1,2-diarylethanes and 1,2- diarylethylenes to 1,2-diaryldiketones

Tetrahedron Letters

Volumn 39, Issue 50, 1998, Pages 9127-9130

  Clayton, Mark D ^a   Marcinow, Zbigniew ^a   Rabideau, Peter W ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AZA ACENAPHTHYLENE; AROMATIC HYDROCARBON; BENZENESELENINIC ANHYDRIDE; CHLOROBENZENE; DIARYL KETONE; DIARYLETHANE; DIARYLETHYLENE; FULLERENE DERIVATIVE; OXIDIZING AGENT; TETRAKETOPYRACENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; OXIDATION; SYNTHESIS;

EID: 0032506576     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02063-2     Document Type: Article

References (15)

1. 1. For some recent reviews on bowl-shaped, fullerene related hydrocarbons, see (a) Siegel, J. S.; Seiders, T. J. Chem. in Britain 1995, 313.
2. (b) Faust, R. Angew. Chem. Internat. Ed. Engl. 1995, 34, 1429.
3. (c) Rabideau, P. W.; Sygula, A. in Advances in Theoretically Interesting Molecules, Vol. 3, Thummel, R. P., Ed. Jai Press Inc., Greenwich, CT, 1995; pp 1-36.
4. (d) Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235.
5. (e) Scott, L. T. Pure Appl. Chem. 1996, 68, 291.
6. 2. Doughty, H. W. J. Am. Chem. Soc. 1909, 41, 326.
7. 3. Ayrey, G.; Barnard, D.; Woodridge, D. T. J. Chem. Soc., 1962, 2089.
8. 4. Barton, D. H. R.; Hui, R. A. H. F.; Lester, D. J.; Ley, S. V. Tetrahedron Lett. 1979, 3331.
9. 5. (a) Clayton, M. D.; Marcinow, Z.; Rabideau, P. W. J. Org. Chem. 1996, 61, 6052.
10. (b) Rabideau, P. W.; Abdourazak, A. H.; Folsom, H. E.; Marcinow, Z.; Sygula, A.; Sygula, R. J. Am. Chem. Soc. 1994, 116, 7891-7892.
11. 9N, 155.0735; found 155.0737.
12. 7. Sakamato, T.; Shiraiwa, M.; Kondo, Y.; Yamanaka, H.; Synthesis 1983, 312.
13. 2, 183.0320; found 183.0324.
14. 9. Kim, T.; Mirafzal, J.; Liu, J.; Bauld, N. L. J. Am. Chem. Soc. 1993, 115, 7653.
15. 10. All starting material is consumed and the product mixture is complex. We also found a number of products with the oxidation of dibenzocyclooctadiene, and the oxidation of dibenzocyclooctatetraene leads, at least in part, to products containing a seven-membered ring. M. D. Clayton and P. W. Rabideau, unpublished results.