Dehydrobenzoannulene-Dimethyldihydropyrene Hybrids: Model Systems for the Synthesis of Molecular Aromatic Probes

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1709-1711

  Kimball, David B ^a   Haley, Michael M ^a   Mitchell, Reginald H ^b   Ward, Timothy R ^b  

^a UNIVERSITY OF OREGON   (United States)

^b UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001755167     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015898r     Document Type: Article

References (28)

1. (a) Haley, M. M. Synlett 1998, 557-565.
2. (b) Haley, M. M.; Pak, J. J.; Brand, S. C. In Topics in Current Chemistry (Carbon-Rich Compounds II); de Meijere, A., Ed.; Springer: Berlin, 1999; Vol. 201, pp 81-130.
3. (a) Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 28, 107-119.
4. (b) Haley, M. M.; Wan, W. B. In Advances in Strained and Interesting Organic Molecules, Volume 8; Halton, B., Ed.; JAI Press: New York, 2000, pp 1-41.
5. (c) Diederich, F. Chem. Commun. 2001, 219-227.
6. (a) Nonlinear Optics of Organic Molecules and Polymers; Nalwa, H. S., Miyata, S., Eds.; CRC Press: New York, 1997.
7. (b) Spreiter, R.; Bosshard, C.; Knöpfle, G.; Günter, P.; Tykwinski, R. R.; Schreiber, M.; Diederich, F. J. Phys. Chem. B 1998, 102, 29-32.
8. (c) Tykwinski, R. R.; Gubler, U.; Martin, R. E.; Diederich, F.; Bosshard, C.; Günter, P. J. Phys. Chem. B 1998, 102, 4451-4465.
9. (d) Sarkar, A.; Pak. J. J.; Rayfield, G. W.; Haley, M. M., submitted.
10. Zhang, D.; Tessier, C. A.; Youngs, W. J. Chem. Mater. 1999, 11, 3050-3057.
11. (a) Balaban, A. T.; Banciu, M.; Ciorba, V. Annulenes, Benzo-, Hetero-, Homo- Derivatives and their Valence Isomers, Vol. 1-3; CRC Press: Boca Raton, 1987.
12. (b) Garratt, P. J. Aromaticity; Wiley: New York, 1986.
13. (c) Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Ya. Aromaticity and Antiaromaticity; Wiley: New York, 1994.
14. (d) Staab, H. A.; Günther, P. Chem. Ber. 1977, 110, 619-630.
15. (a) Kimball, D. B.; Wan, W. B.; Haley, M. M. Tetrahedron Lett. 1998, 39, 6795-6798.
16. (b) Matzger, A. J.; Vollhardt, K. P. C. Tetrahedron Lett. 1998, 39, 6791-6794.
17. (c) Bell, M. L.; Chiechi, R. C.; Johnson, C. A.; Kimball, D. B.; Matzger, A. J.; Wan, W. B.; Weakley, T. J. R.; Haley, M. M. Tetrahedron, in press.
18. (d) Wan, W. B.; Chiechi, R. C.; Weakley, T. J. R.; Haley, M. M., submitted.
19. 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.
20. Mitchell, R. H.; Iyer, V. S. J. Am. Chem. Soc. 1996, 118, 2903-2906 and references therein.
21. (a) Mitchell, R. H.; Venugopalan, S.; Zhou, P.; Dingle, T. W. Tetrahedron Lett. 1990, 31, 5281-5284.
22. (b) Mitchell, R. H.; Chen, Y. Tetrahedron Lett. 1996, 37, 5239-5242.
23. (a) Mitchell, R. H.; Ward, T. R.; Wang, Y.; Dibble, P. W. J. Am. Chem. Soc. 1999, 121, 2601-2602.
24. (b) Marsella, M. J.; Wang, Z.-Q.; Mitchell, R. H. Org. Lett. 2000, 2, 2979-2982.
25. Tashiro, M.; Yamato, T. Chem. Lett. 1980, 1127-1130.
26. Sjögren, M.; Hansson, S.; Norrby, P.-O.; Akermark, B.; Cucciolito, M. E.; Vitagliano, A. Organometallics 1992, 11, 3954-3964.
27. Cai, C.; Vasella, A. Helv. Chim. Acta 1995, 78, 2053-2064.
28. Steric interactions with the pyrene protons and the tert-butyl groups prevent accurate comparisons of the bay protons on 1 and 5 (as determined by modeling on Spartan).