Synthesis of Benzo-Fused Tetraphenylenes and Crystal Structure of a 4:1 Clathrate Inclusion Compound of Dibenzo[b,h]tetraphenylene with p-Xylene

Journal of Organic Chemistry

Volumn 55, Issue 10, 1990, Pages 3214-3221

  Man, Yuet Ming ^a   Mak, Thomas C W ^a   Wong, Henry N C ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000366894     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00297a043     Document Type: Article

References (32)

1. Arene Synthesis by Extrusion Reaction. 14. Part 13: Wong, T.; Cheung, S. S.; Wong, H. N. C. Angew. Chem., Int. Ed. Engl. 1988, 27, 705–706.
2. For a review on the synthesis of novel benzenoid molecules by low-valent-titanium deoxygenation, see: Wong, H. N. C. Acc. Chem. Res. 1989, 22, 145–152.
3. For enantiomer resolution and measurement of the barrier to ring inversion for compound 6, see: Rashidi-Ranjbar, P.; Man, Y.-M.; Sandstrom, J.; Wong, H. N. C. J. Org. Chem. 1989, 54, 4888–4892.
4. Also known as Nai Zheng Huang. To whom correspondence should be addressed.
5. Mak, T. C. W.; Wong, H. N. C. Top. Curr. Chem. 1987, 140, 141–164.
6. Rapson, W. S.; Shuttleworth, R. G.; van Niekerk, J. N. J. Chem. Soc. 1943. 326–327.
7. Huang, N. Z.; Mak, T. C. W. J. Chem. Soc., Chem. Commun. 1982, 543–544.
8. Chan, T.-L.; Mak, T. C. W.; Trotter, J. J. Chem. Soc., Perkin Trans. 2 1980, 672–675.
9. Czugler, M.; Kalman, A. J. Mol. Struct. 1981, 75, 29–37.
10. Wittig, G.: Lehmann, G. Chem. Ber. 1957, 90, 875–892.
11. Wittig, G.: Klar, G. Justus Liebigs Ann. Chem. 1967, 704, 91–108.
12. Wittig, G.; Bickelhaupt, F. Chem. Ber. 1958, 91, 883–894.
13. Cade, J. A.: Pilbeam, A. J. Chem. Soc. 1964. 114–121.
14. Chatt, J.; Guy, R. G.; Watson, H. R. J. Chem. Soc. 1961. 2332–2335.
15. Lindow, D. F.; Friedman, L. J. Am. Chem. Soc. 1967, 89, 1271–1272.
16. Friedman, L.; Lindow, D. F. J. Am. Chem. Soc. 1968, 90, 2324–2328.
17. Wong, H. N. C.; Sondheimer, F. Tetrahedron 1981, 37 (Si), 99–109.
18. Xing, Y. D.: Huang, N. Z. J. Org. Chem. 1982, 47, 140–142.
19. Ried, W.; Bodem, H. Chem. Ber. 1956, 89, 708–712.
20. Hebbelynck, M. F.; Martin, R. H. Bull. Soc. Chim. Belg. 1950, 59, 193–207.
21. Cava, M. P.; Hsu, A.-F. C. J. Am. Chem. Soc. 1972, 94, 6441–6444.
22. Narayanan, C. R.; Iyer, K. N. Tetrahedron Lett. 1964, 759–763.
23. Rynard, C. M.; Thankachan, C.; Tidwell, T. T. J. Am. Chem. Soc. 1979, 101, 1196–1201.
24. Naito, K.; Rickborn, B. J. Urg. Chem. 1980, 45, 4061–4062.
25. Chan, T.-L.; Huang, N. Z.; Sondheimer, F. Tetrahedron 1983, 39, 427–432.
26. Wong, H. N. C.; Man, Y.-M.; Mak, T. C. W. Tetrahedron Lett. 1987. 28. 6359–6362.
27. Irngartinger, H.; Reibel, W. R. K. Acta Crystallogr., Sect. B 1981, 37, 1724–1728.
28. Sparks, R. A. In Crystallographic Computing Techniques: Ahmed, F. R., Ed.; Munksgaard; Copenhagen, 1976; p 452.
29. Diamond, R. Acta Crystallogr., Sect. A 1969, A25, 43–45.
30. Kopfmann, F.; Huber, R. Acta Crystallogr., Sect. A 1968, A24, 348–351.
31. Sheldrick, G. M. In Computational Crystallography; Sayre, D., Ed.; Oxford University Press: New York, 1982; p 506.
32. International Tables for X-Ray Crystallography; Kynoch Press: Birmingham (now distributed by Kluwer Academic Publishers, Dordrecht), 1973; Vol. IV, pp 55–99, 149.