Bond fixation in a [14]annulene: Synthesis, characterization, and ab initio computations of furan adducts of dimethyldihydropyrene

Journal of the American Chemical Society

Volumn 118, Issue 12, 1996, Pages 2907-2911

  Mitchell, Reginald H ^a   Chen, Yongsheng ^a   Iyer, Vivekanantan S ^a   Lau, Danny Y K ^a   Baldridge, Kim K ^b   Siegel, Jay S ^c  

^a UNIVERSITY OF VICTORIA   (Canada)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000590728     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953795w     Document Type: Article

References (33)

1. (a) Bürgi, H.-B.; Baldridge, K. K.; Hardcastle, K.; Frank, N. L.; Gantzel, P., Siegel, J. S.; Ziller, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1454.
2. (b) Frank, N. L.; Baldridge, K. K.; Gantzel, P.; Siegel, J. S. Tetrahedron Lett. 1995, 36, 4389.
3. (c) Frank, N. L.; Baldridge, K. K.; Siegel, J. S J. Am. Chem. Soc. 1995, 117, 2102.
4. Kohnke, F. H.; Mathias, J. P.; Stoddart, J. F.; Slawin, A. M. Z.; Williams, D. J. Acta Crystallogr., Sect. C 1992, C48, 663.
5. Such bond localization has historically been related to a so-called "Mills-Nixon" effect. Careful reading of the original literature makes it abundantly clear that Mills and Nixon's work does not apply in a modern structural context and any attribution of modern experimental observations to "Mills-Nixon" effects is a misnomer. For a more detailed analysis, see: (a) Siegel, J. S. Angew. Chem. Int. Ed. Engl. 1994, 33, 1721. (b) Frank, N. L.; Siegel, J. S. Adv. Theor. Interesting Mol. 1989, 3, 209-260.
6. Such bond localization has historically been related to a so-called "Mills-Nixon" effect. Careful reading of the original literature makes it abundantly clear that Mills and Nixon's work does not apply in a modern structural context and any attribution of modern experimental observations to "Mills-Nixon" effects is a misnomer. For a more detailed analysis, see: (a) Siegel, J. S. Angew. Chem. Int. Ed. Engl. 1994, 33, 1721. (b) Frank, N. L.; Siegel, J. S. Adv. Theor. Interesting Mol. 1989, 3, 209-260.
7. Mitchell, R. H. Adv. Theor. Interesting Mol. 1989, 1, 135-199.
8. Mitchell, R. H., Iyer, V. S.; Khalifa, N.; Mahadevan, R.; Venugopalan, S.; Weerawarna, S. A.; Zhou, P. J. Am. Chem Soc. 1995, 117, 1514-1532.
9. Mitchell, R. H.; Slowey, P. D., Kamada, T.; Williams, R. V.; Garratt, P. J. J. Am. Chem. Soc. 1984, 106, 2431-2432
10. Mitchell, R. H.; Lau, D. Y. K., Iyer, V. S. Unpublished results.
11. Phillips, J. B.; Molyneux, R. J., Sturm, E.; Boekelheide, V. J. Am. Chem. Soc. 1967, 89, 1704-1709. Prepared by reaction of 1 with 2 equiv of NBS in dry DMF (see: Mitchell, R. H., Lai, Y. H.; Williams, R. V. J. Org. Chem. 1979, 44, 4733-4735).
12. Phillips, J. B.; Molyneux, R. J., Sturm, E.; Boekelheide, V. J. Am. Chem. Soc. 1967, 89, 1704-1709. Prepared by reaction of 1 with 2 equiv of NBS in dry DMF (see: Mitchell, R. H., Lai, Y. H.; Williams, R. V. J. Org. Chem. 1979, 44, 4733-4735).
13. Mitchell, R. H.; Williams, R. V.; Dingle, T. W. J. Am. Chem. Soc. 1982, 104, 2560-2571.
14. (a) Haddon, R. C.; Raghavachari, K. J. Am. Chem. Soc. 1982, 104, 3516-3518.
15. (b) Haddon, R. C.; Raghavachari, K. J. Am. Chem. Soc. 1985, 107, 289-297.
16. (c) Xie, Y.; Schaefer, H. F., III; Liang, G.; Bowen, J. P. J. Am. Chem. Soc. 1994, 116, 1442-1449.
17. (d) Baumann, H. J. Am. Chem. Soc. 1978, 100, 7196.
18. For a related orbital analysis, see: (a) Jorgensen, W. L.; Borden, W. T. J. Am. Chem. Soc. 1973, 95, 6649. (b) Gleiter, R.; Bischof, P.; Gubernator, K.; Christi, M., Schwager, L.; Vogel, P. J. Org. Chem. 1985, 50, 5064. (c) Gleiter, R.; Heilbronner, E.; Heckman, M.; Martun, H.-D. Chem. Ber. 1973, 106, 28.
19. For a related orbital analysis, see: (a) Jorgensen, W. L.; Borden, W. T. J. Am. Chem. Soc. 1973, 95, 6649. (b) Gleiter, R.; Bischof, P.; Gubernator, K.; Christi, M., Schwager, L.; Vogel, P. J. Org. Chem. 1985, 50, 5064. (c) Gleiter, R.; Heilbronner, E.; Heckman, M.; Martun, H.-D. Chem. Ber. 1973, 106, 28.
20. For a related orbital analysis, see: (a) Jorgensen, W. L.; Borden, W. T. J. Am. Chem. Soc. 1973, 95, 6649. (b) Gleiter, R.; Bischof, P.; Gubernator, K.; Christi, M., Schwager, L.; Vogel, P. J. Org. Chem. 1985, 50, 5064. (c) Gleiter, R.; Heilbronner, E.; Heckman, M.; Martun, H.-D. Chem. Ber. 1973, 106, 28.
21. (a) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1982, 28, 213.
22. (b) Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163.
23. (a) Dunning, T. H. J. Chem. Phys. 1971, 55, 716.
24. (b) McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
25. (c) Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033.
26. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Jensen, J. H.; Koseki, S.; Gordon, M. S.; Nguyen, K. A.; Windus, T. L.; Elbert, S. T. QCPE Bull. 1990, 10, 52.
27. Pople, J. A., Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1.
28. GAUSSIAN 92, Revision C, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, J. A. Pople; Gaussian, Inc.: Pittsburgh, PA. 1992.
29. (a) Amos, R. D.; Rice, J. E. CADPAC: The Cambridge Analytic Derivatives Pasckage, Issue 5.2, Cambridge, 1995.
30. (b) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
31. (c) Lee, C.; Yang, W.; Parr, R G. Phys. Rev. B 1988, 37, 785.
32. (d) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
33. (e) Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244.