Deantiaromatization as a driving force in an electrocyclic reaction

Angewandte Chemie - International Edition

Volumn 45, Issue 12, 2006, Pages 1966-1971

  Harmata, Michael ^a   Zheng, Pinguan ^a   Schreiner, Peter R ^b   Navarro Vázquez, Armando ^c  

^a UNIVERSITY OF MISSOURI   (United States)

^b JUSTUS LIEBIG UNIVERSITY   (Germany)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Antiaromaticity; Computational chemistry; Cyclopentadienones; Electrocyclization; Hamigeran B

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; REACTION KINETICS; REDOX REACTIONS; SYNTHESIS (CHEMICAL);

ANTIAROMATICITY; COMPUTATIONAL CHEMISTRY; CYCLOPENTADIENONES; ELECTROCYCLIZATION; HAMIGERAN B;

KETONES;

EID: 84962361553     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503812     Document Type: Article

References (39)

1. a) K. B. Wiberg, Chem. Rev. 2001, 101, 1317;
2. b) A. D. Allen, T. T. Tidwell, Chem. Rev. 2001, 101, 1333;
3. c) R. Breslow, Acc. Chem. Res. 1973, 6, 393.
4. a) G. Maier, Angew. Chem. 1988, 100, 317;
5. Angew. Chem. Int. Ed. Engl. 1988, 27, 309;
6. b) T. Bally, S. Masamune, Tetrahedron 1980, 36, 343;
7. c) A. Efraty, Chem. Rev. 1977, 77, 691;
8. d) G. Maier, Angew. Chem. 1974, 86, 491;
9. Angew. Chem. Int. Ed. Engl. 1974, 13, 425.
10. M. A. Ogliaruso, M. G. Romanelli, E. I. Becker, Chem. Rev. 1965, 65, 261.
11. a) J. Limanto, K. S. Khuong, K. N. Houk, M. L. Snapper, J. Am. Chem. Soc. 2003, 125, 16 310;
12. b) J. Limanto, J. A. Tallarico, J. R. Porter, K. S. Khuong, K. N. Houk, M. L. Snapper, J. Am. Chem. Soc. 2002, 124, 14 748;
13. c) J. Limanto, M. L. Snapper, J. Am. Chem. Soc. 2000, 122, 8071;
14. d) J. Limanto, M. L. Snapper, J. Org. Chem. 1998, 63, 6440;
15. e) J. A. Tallarico, M. L. Randall, M. L. Snapper, J. Am. Chem. Soc. 1996, 118, 9196.
16. M. Harmata, C. L. Barnes, J. Brackley, G. Bohnert, P. Kirchhoefer, L. Kürti, P. Rashatasakhon, J. Org. Chem. 2001, 66, 5232.
17. However, we were aware, of course, that the paths to 4 and 5 were fundamentally different, the former being directly analogous to an electrocyclization of an octatetraene (conrotatory) and the latter being analogous to an electrocyclization of hexatriene (disrotatory). Other things being equal, it is well known that the former electrocyclization proceeds much more rapidly than the latter, so that a competition between the two should favor the conrotatory [8π] electrocyclization; for examples and references, see: a) B. Lecea, A. Arrieta, F. P. Cossío, J. Org. Chem. 2005, 70, 1035;
18. b) S. Sakai, S.-y. Takane, J. Phys. Chem. A 1999, 103, 2878.
19. a) B. B. Kikani, J. R. McKee, M. Zanger, Synthesis 1991, 176;
20. b) W. C. Black, C. Brideau, C.-C. Chan, S. Charleson, N. Chauret, D. Claveau, D. Ethier, R. Gordon, G. Greig, J. Guay, G. Hughes, P. Jolicoeur, Y. Leblanc, D. Nicoll-Griffith, N. Ouimet, D. Riendeau, D. Visco, Z. Wang, L. Xu, P. Prasit, J. Med. Chem. 1999, 42, 1274.
21. a) B. A. Narayanan, W. H. Bunnelle, Tetrahedron Lett. 1987, 28, 6261;
22. b) M. T. Crimmins, D. Dedopoulou, Synth. Commun. 1992, 22, 1953.
23. 13C NMR spectra of 10 matched those in the literature: K. K. De Fonseka, J. J. McCullough, A. J. Yarwood, J. Am. Chem. Soc. 1979, 101, 3277.
24. CCDC-285 951 (9) and -285952 (17) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
25. a) F. G. West, G. U. Gunawardena, J. Org. Chem. 1993, 58, 5043;
26. b) G. U. Gunawardena, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1997, 119, 2066.
27. J. Gräfenstein, E. Kraka, M. Filatov, D. Cremer, Int. J. Mol. Sci. 2002, 3, 360.
28. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648;
29. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
30. W. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
31. P. R. Schreiner, A. Navarro-Vázquez, M. Prall, Acc. Chem. Res. 2005, 38, 29.
32. S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117.
33. Gaussian03, Revision B.05, M. J. Frisch et al., Gaussian, Inc., Wallingford, CT, 2004.
34. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. v. E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317.
35. K. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251.
36. http://www.chemistry.mcmaster.ca/aimpac.
37. P. Quadrelli, S. Romano, L. Toma, P. Caramella, J. Org. Chem. 2003, 68, 6035.
38. K. Najafian, P. v. R. Schleyer, T. T. Tidwell, Org. Biomol. Chem. 2003, 1, 3410.
39. D. L. J. Clive, J. Wang, Org. Prep. Proced. Int. 2005, 37, 1.