DFT calculation on the stereochemistry of the allylic oxidation. Selenium dioxide-mediated oxidation of an exocyclic olefinic hydrindane compound

Bulletin of the Korean Chemical Society

Volumn 29, Issue 12, 2008, Pages 2513-2516

  Ra, Choon Sup ^a   Park, Eun Mook ^a   Park, Gyoosoon ^b  

^a Yeungnam University   (South Korea)

^b Kookmin University   (South Korea)

Author keywords

Ab initio calculation; Allylic oxidation; Hydrindane; Selenium dioxide; Stereochemistry

Indexed keywords

EID: 60149101083     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2008.29.12.2513     Document Type: Article

References (23)

1. For reviews: Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 83.
2. Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986.
3. Wilkinson, S. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p 579.
4. Rabjohn, N. Org. React. 1978, 24, 261.
5. Campbell, T. W.; Walker, H. G.; Coppinger, G. M. Chem. Rev. 1952, 50, 279.
6. Rabjohn, N. Org. React. 1949, 5, 331.
7. Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
8. Examples for the synthetic applications: Fairlamb, I. J. S.; Dickinson, J. M.; Pegg, M. Tetrahedron Lett. 2001, 42, 2205.
9. Tauber, A. Y.; Hynninen, P. H. Tetrahedron Lett. 1993, 34, 2979.
10. Kshirsagar, T. A.; Moe, S. T.; Portoghese, P. S. J. Org. Chem. 1998, 63, 1704.
11. Madec, D.; Ferezou, J. P. Synlett 1996, 867.
12. Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404.
13. de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 11809 and references therein.
14. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1978, 100, 3435.
15. Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404.
16. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1972, 94, 7154.
17. Arigoni, D.; Vasella, A.; Sharpless, K. B.; Jensen, H. P. J. Am. Chem. Soc. 1973, 95, 7917.
18. Singleton, D. A.; Hang, C. J. Org. Chem. 2000, 65, 7554.
19. Ra, C. S.; Park, G. Tetrahedron Lett. 2003, 44, 1099.
20. Frisch, M. J. et al. Gaussian 03, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
21. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
22. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
23. The energies of transition states are not accounted for the zero-point energy.