Unusual photorearrangements of 9,10-disubstituted triptycene-1,4-quinone derivatives

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2121-2124

  Borecka, Bozena ^a   Gamlin, Janet N ^a   Gudmundsdottir, Anna D ^a   Olovsson, Gunnar ^a   Scheffer, John R ^a   Trotter, James ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

TRIPTYCENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029991942     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00231-6     Document Type: Article

References (22)

1. Fu, T.Y.; Gamlin, J.N., Olovsson, G.; Scheffer, J.R.; Trotter, J. and Young, D.T. Tetrahedron Lett. 1995, 36, 2025.
2. Mylorie, V.L.; Stenberg, J.F. Ann. N.Y. Acad. Sci. 1973, 214, 255.
3. Theilacker, W.; Berger-Brose, U.; Beyer, K-H. Chem. Ber. 1960, 93, 1658.
4. Miller, M.W.; Amidon, R.W.; Tawney, P.O. J. Am. Chem. Soc. 1955, 77, 2845.
5. 1/n, a = 8.114(3) Å, b = 11.966(3) Å, c = 16.694 Å, Z = 4, R = 3.7%. Full crystallographic details will be published separately.
6. 2: C, 84.59, H, 5.16. Found: C, 84.19; H, 5.13.
7. 4: C, 77.40; H, 5.41. Found: C, 77.28; H, 5.25.
8. Our best guess is that this material is a phenolic aldehyde having the benz[a]aceanthrylene carbon skeleton. Benz[a]aceanthrylene derivatives are commonly observed byproducts in the photochemistry of triptycenes. See, for example, Kawada, Y.; Tukada, H.; Iwamura, H. Tetrahedron Lett. 1980, 21, 181 and references cited therein.
9. For additional examples of the strong effect that bridgehead substitution has on the photochemistry of 9,10-ethenoanthracene derivatives, see Scheffer, J.R.; Trotter, J.; Yang, J. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W.M.; Song, P-S. Eds.; CRC Press: Boca Raton, Florida, 1995, Chapter 16.
10. Walsh, T.D. J. Am. Chem. Soc. 1969, 91, 515.
11. Turro, N.J.;Tobin, M; Friedman, L.; Hamilton, J.B. J. Am. Chem. Soc. 1969, 91, 516.
12. (a) Iwamura, H.; Yoshimura, K. J. Am. Chem. Soc. 1974, 96, 2652;
13. (b) Iwamura, M.; Tukada, H.; Iwamura, H. Tetrahedron Lett. 1980, 21, 4865.
14. For reviews of the di-π-methane rearrangement, see (a) Zimmerman, H.E. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Chapter 16;
15. (b) Zimmerman, H.E. In Organic Photochemistry, Padwa, A., Ed.; Marcel Dekker: New York, 1991; Volume 11, Chapter 1. The preference for initial benzo-quino bridging as opposed to benzo-benzo bridging is the same as that observed for quinone 1a (see reference 1) and is in accord with formation of the more stable biradical intermediate in which aromaticity has been lost in only one of the two benzenoid rings and the second odd electron is stabilized by being next to a carbonyl group.
16. For a recent review of the Norrish/Yang type Il photoreaction, see Wagner, P.J.; Park, B-S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Volume 11, Chapter 4.
17. Orlando, C.M.; Mark, H.; Bose, A.K.; Manhas, M.S. J. Am. Chem. Soc. 1967, 89, 6527.
18. Scheffer, J.R. In Organic Solid State Chemistry, Desiraju, G.R., Ed.; Elsevier: New York, 1987; Chapter 1.
19. (a) Iwamura, H.; Tukada, H. J. Chem. Soc., Chem. Commun. 1975, 969;
20. (b) Day, R.O.; Day, V.W.; Fuerniss, S.J.; Hohman, J.R.; Wheeler, D.M.S. J. Chem. Soc., Chem. Commun., 1976, 853;
21. (c) Iwamura, M.; Mori, E.; Koike, A.; Kitagawa, T.; Koga, N.; Iwamura, H. Chem. Lett. 1992, 2051 and references cited therein.
22. Prepared by standard procedures, mp 174-176 °C. Gudmundsdottir, A.D.; Scheffer, J.R. unpublished results.