Synthesis and optical resolution of 9,9′-spirobifluorene-1,1′- diol

Organic Letters

Volumn 6, Issue 14, 2004, Pages 2381-2383

  Cheng, Xu ^a   Hou, Guo Hua ^a   Xie, Jian Hua ^a   Zhou, Qi Lin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; ENANTIOMER; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; OPTICAL DENSITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 3242665486     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0492546     Document Type: Article

References (39)

1. (a) Tour, J. M.; Wu, R.-L.; Schumm, J. S. J. Am. Chem. Soc. 1990, 112, 5662.
2. (b) Pei, J.; Ni, J.; Zhou, X.-H.; Cao, X.-Y.; Lai, Y.-H. J. Org. Chem. 2002, 67, 8112.
3. (a) Bach, U.; Lupo, D.; Comte, P.; Moser, J. E.; Weissortel, F.; Salbeck, J.; Spreitzer, H.; Gratzel, M. Nature 1998, 395, 583.
4. (b) Schartel, B.; Damerau, T.; Hennecke, M. Phys. Chem. Chem. Phys. 2000, 2, 4690.
5. (c) Wu, C. C.; Lin, Y. T.; Chiang, H. H.; Cho, T. Y.; Chen, C. W. Appl. Phys. Lett. 2002, 81, 577.
6. (d) Chien, Y.-Y.; Wong, K.-T.; Chou, P.-T.; Cheng, Y.-M. Chem. Commun. 2002, 2874.
7. (e) Krüger, J.; Plass, R.; Grätzel, M.; Cameron, P. J.; Peter, L. M. J. Phys. Chem. B 2003, 107, 7536.
8. (f) Lee, J.-I.; Lee, H.; Oh, J.; Chu, H. Y.; Kim, S. H.; Yang, Y. S.; Kim, G. H.; Do, L.-M.; Zyung, T. Curr. Appl. Phys. 2003, 3, 469.
9. (a) Smith, D. K.; Diederich, F. J. Chem. Soc., Chem. Commun. 1998, 2501.
10. (b) Lustenberger, P.; Martinborough, E.; Denti, T. M.; Diederich, F. J. Chem. Soc., Perkin Trans. 2 1998, 747.
11. (c) Smith, D. K.; Zingg, A.; Diederich, F. Helv. Chim. Acta 1999, 82, 1225.
12. (d) Tejeda, A.; Oliva, A. I.; Simón, L.; Grande, M.; Caballero, M.-C.; Morán, J. R. Tetrahedron Lett. 2000, 41, 4563.
13. (a) Fournier, J.-H.; Maris, T.; Wuest, J. D. J. Org. Chem. 2003, 68, 241.
14. (b) Poriel, C.; Ferrand, Y.; Le Maux, P.; Raul-Berthelot, J.; Simonneaux, G. Chem. Commun. 2003, 1105.
15. (c) Poriel, C.; Ferrand, Y.; Le Maux, P.; Paul, C.; Rault-Berthelot, J.; Simonneaux, G. Chem. Commun. 2003, 2308.
16. (d) Pei, J.; Ni, J.; Zhou, X.-H.; Cao, X.-Y.; Lai, Y.-H. J. Org. Chem. 2002, 67, 4924.
17. (e) Shu, C.-F.; Wu, S.-C. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1160.
18. (f) Reddy, D. S.; Chou, C.-H.; Shu, C.-F.; Lee, G.-H. Polymer 2003, 44, 557.
19. (a) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180.
20. (b) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Org. Synth. 1998, 76, 6.
21. (c) Yuyet, T. M. T.; Harada, T.; Hashimoto, K.; Hatsuda, M.; Oku, A. J. Org. Chem. 2000, 65, 1335.
22. (a) Prelog, V. Pure Appl. Chem. 1978, 50, 893.
23. (b) Prelog, V.; Bedeković, D. Helv. Chim. Acta 1979, 62, 2285.
24. Weisburger, J. H.; Weisburger, E. K.; Ray, F. E. J. Am. Chem. Soc. 1950, 72, 4250.
25. PPA = polyphosphoric acid.
26. Though excess pyridine was present, the ring closure is complete at 0°C in 5 min.
27. Tilly, D.; Samanta, S. S.; Faigl, F.; Mortier, J. Tetrahedron Lett. 2002, 43, 8347.
28. (a) Birman, V. B.; Rheingold, A. L.; Lam, K.-C. Tetrahedron: Asymmetry 1999, 10, 125.
29. (b) Zhu, S.-F.; Fu, Y.; Xie, J.-H.; Liu, B.; Xing, L.; Zhou, Q.-L. Tetrahedron: Asymmetry 2003, 14, 3219.
30. (a) Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Academic Press: London, 1984; Vols. 1-111; Oxford University Press: Oxford, 1991; Vols. IV, V.
31. (a) Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Academic Press: London, 1984; Vols. 1-111; Oxford University Press: Oxford, 1991; Vols. IV, V.
32. (b) Molecular Inclusion and Molecular Recognition-Clathrates I and II; Weber, E., Ed.; Topics in Current Chemistry; Springer: Berlin, 1987, 1988; Vols. 140, 149.
33. (c) Tanaka, K.; Okada, T.; Toda, F. Angew. Chem., Int. Ed. Engl. 1993, 32, 1147.
34. (d) Toda, F.; Tanaka, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1994, 59, 5748.
35. (e) Toda, F.; Tanaka, K., Chem. Commun. 1997, 1087.
36. (f) Ding, K.; Wang, Y.; Yun, H.; Liu, J.; Wu, Y.; Terada, M.; Okubo, Y.; Mikami, K. Chem. Eur. J. 1999, 5, 1734.
37. (g) Periasamy, M.; Venkatraman, L.; Thomas, K. R. J. J. Org. Chem. 1997, 62, 4302.
38. Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
39. 1 = 0.0687. For crystallographic data for the structure, see the Supporting Information.