Synthesis of the elusive dibenzannelated dihydropyrene dibenzo[e,l]dimethyldihydropyrene, a molecular photo-switch

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5239-5242

  Mitchell, Reginald H ^a   Chen, Yongsheng ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; POLYCYCLIC AROMATIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; THERMODYNAMICS;

EID: 0030598042     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01074-X     Document Type: Article

References (20)

1. 1. Mitchell, R. H.; Carruthers, R. J. Tetrahedron Lett. 1975, 16, 4331-4334.
2. 2. Mitchell, R. H.; Yan, J. S. H. Can. J. Chem. 1977, 55, 3347-3348; Mitchell, R. H.; Carruthers, R. J.; Mazuch, L. J. Am. Chem. Soc. 1978, 100, 1007-1008.
3. 2. Mitchell, R. H.; Yan, J. S. H. Can. J. Chem. 1977, 55, 3347-3348; Mitchell, R. H.; Carruthers, R. J.; Mazuch, L. J. Am. Chem. Soc. 1978, 100, 1007-1008.
4. 3. 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.
5. 4. (a) Mitchell, R.H.; Iyer, V.S.; Mahadevan, R.; Venugopalan, S.; Zhou, P. J. Org. Chem. 1996, in press;
6. (b) Mitchell, R.H.; Carruthers, R.J.; Mazuch, L.; Dingle, T.W. J. Am. Chem. Soc. 1982, 104, 2544-2551.
7. (c) Mitchell, R.H.; Yan, J.S.H.; Dingle, T.W. J. Am. Chem. Soc. 1982, 104, 2551-2559.
8. 5. Blattmann, H. R.; Meuche, D.; Heilbronner, E.; Molyneux, R. J., Boekelheide, V. J. Am. Chem. Soc. 1965, 87, 130-131; Blattmann, H. R.; Schmidt, W. Tetrahedron, 1970, 26, 5885-5899.
9. 5. Blattmann, H. R.; Meuche, D.; Heilbronner, E.; Molyneux, R. J., Boekelheide, V. J. Am. Chem. Soc. 1965, 87, 130-131; Blattmann, H. R.; Schmidt, W. Tetrahedron, 1970, 26, 5885-5899.
10. 6. Weerawarna, S. A. Ph. D. Thesis, University of Victoria, April 1988.
11. 7. Mitchell, R. H.; Weerawarna, S. A. Tetrahedron Lett. 1986, 27, 453-456.
12. 8. Mitchell, R. H.; Zhou, P. Tetrahedron Lett. 1990, 37, 5277-5280.
13. 9. Tashiro, M.; Yamato, T. J. Am. Chem. Soc. 1982, 104, 3701-3707.
14. 10. Mitchell, R. H.; Lai, Y. H.; Williams, R. V. J. Org. Chem. 1979, 44, 4733-4735.
15. 4 was not so successful, see: Miyazawa, A.; Yamato, T.; Tashiro, M. J. Org. Chem. 1991, 56, 1334-1337.
16. max) 377 (53,000), 391 (36,100), 446 (6,900), 665 (800). The more soluble isomer, two syn oxygen bridges, showed internal methyl protons at δ -3.70 and -4.30.
17. 13C NMR (90.6 MHz) δ 150.9, 144.6, 140.6, 138.9, 129.4, 129.2, 129.0, 34.7, 31.6, 18.7.
18. 14. Mitchell, R. H. Org. Chem. (Academic Press), 1983, 45, 239-310.
19. max) 301 (63,000), 327 (80,000), 340 (79,000), 407 (67,000), 431 (154,000), 625 (ca 8,000), 680 (ca 8,000) 730 (ca 4,000).
20. 16. Mitchell, R. H.; Williams, R. V.; Dingle, T. W. J. Am. Chem. Soc. 1982, 104, 2560-2571.