Thermal cycloaddition facilitated by orthogonal π-π organization through conformational transfer in a swivel-cruciform oligo(phenylenevinylene)

Angewandte Chemie - International Edition

Volumn 46, Issue 18, 2007, Pages 3245-3248

  Tian, Leilei ^a   He, Feng ^a   Zhang, Houyu ^a   Xu, Hai ^a   Yang, Bing ^a   Wang, Chunyu ^a   Lu, Ping ^a   Hanif, Muddasir ^a   Li, Fei ^a   Ma, Yuguang ^a   Shen, Jiacong ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

Biaryls; Conformation analysis; Cycloaddition; Regioselectivity; Stereoselectivity

Indexed keywords

CHEMICAL BONDS; CONFORMATIONS; CYCLOADDITION; MOLECULAR DYNAMICS; REGIOSELECTIVITY; STEREOSELECTIVITY;

CONFORMATION ANALYSIS; INTRAMOLECULAR CYCLOADDUCT; ROOM TEMPERATURE;

VINYL RESINS;

EID: 34250888148     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603878     Document Type: Article

References (54)

1. a) R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797;
2. Angew. Chem. Int. Ed. Engl. 1969, 8, 781;
3. b) R. B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 1965, 87, 395;
4. c) R. B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 1965, 87, 2046;
5. d) R. B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 1965, 87, 2511;
6. e) R. B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, Velag Chemie, New York, 1970;
7. f) N. D. Epiotis, B. L. Yates, D. Carlberg, F. Bernardi, J. Am. Chem. Soc. 1976, 98, 453;
8. g) N. D. Epiotis, Angew. Chem. 1974, 86, 825;
9. Angew. Chem. Int. Ed. Engl. 1974, 13, 751.
10. a) A. Padwa, T. J. Blacklock, J. Am. Chem. Soc. 1979, 101, 3390;
11. b) H. Meier, Angew. Chem. 1992, 104, 1425;
12. Angew. Chem. Int. Ed. Engl. 1992, 31, 1399;
13. c) A. Padwa, W. Koehn, J. Masaracchia, C. L. Osborn, D. J. Trecker, J. Am. Chem. Soc. 1971, 93, 3633;
14. d) F. D. Lewis, T. I. Ho, R. DeVoe, J. Org. Chem. 1980, 45, 5283;
15. e) N. D. McClenaghan, C. Absalon, D. M. Bassani, J. Am. Chem. Soc. 2003, 125, 13004;
16. f) D. G. Amirsakis, A. M. Elizarov, M. A. Garcia-Garibay; P. T. Glink, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2003, 115, 1158;
17. Angew. Chem. Int. Ed. 2003, 42, 1126;
18. g) E. Galoppini, R. Chebolu, R. Gilardi, W. Zhang, J. Org. Chem. 2001, 66, 162.
19. a) F. H. Allen, M. F. Mahon, P. R. Raithby, G. P. Shields, H. A. Sparkes, New J. Chem. 2005, 29, 182;
20. b) V. Ramamurthy, K. Venkatesan, Chem. Rev. 1987, 87, 433;
21. c) S. Ohba, H. Hosomi, Y. Ito, J. Am. Chem. Soc. 2001, 123, 6349;
22. d) D. B. Varshney, G. S. Papaefstathiou, L. R. MacGillivray, Chem. Commun. 2002, 1964;
23. e) H. M. Sheldrake, T. W. Wallace, C. P. Wilson, Org. Lett. 2005, 7, 4233.
24. S. Y. Jon, Y. H. Ko, S. H. Park, H. J. Kim, K. Kim, Chem. Commun. 2001, 1938.
25. a) M. D. Cohen, G. M. J. Schmidt, F. I. Sonntag, J. Chem. Soc. 1964, 2000;
26. b) G. M. J. Schmidt, J. Chem. Soc. 1964, 2014.
27. C.-H. Tung, L.-Z. Wu, L.-P. Zhang, A. B. Chen, Acc. Chem. Res. 2003, 36, 39.
28. W. Herrmann, S. Wehrle, G. Wenz, Chem. Commun. 1997, 1709.
29. K. Takaoka, M. Kawano, T. Ozeki, M. Fujita, Chem. Commun. 2006, 1625.
30. a) H. Maeda, K. Nishimura, K. Mizuno, M. Yamaji, J. Oshima, S. Tobita, J. Org. Chem. 2005, 70, 9693;
31. b) C. W. Susan, A. F. Steven, J. Org. Chem. 1994, 59, 6476.
32. a) A. A. Borisenko, A. V. Nikulin, S. Wolfe, N. S. Zefirov, N. V. Zyk, J. Am. Chem. Soc. 1984, 106, 1074;
33. b) P. Alvarez, E. Lastra, J. Gimeno, M. Bassetti, L. R. Falvello, J. Am. Chem. Soc. 2003, 125, 2386;
34. c) P. Brana, J. Gimeno, J. A. Sordo, J. Org. Chem. 2004, 69, 2544;
35. d) B. Lecea, A. Arrieta, I. Arrastia, F. P. Cossio, J. Org. Chem. 1998, 63, 5216;
36. e) M. Alajarín, A. Vidal, F. Tovar, A. Arrieta, B. Lecea, F. P. Cossio, Chem. Eur. J. 1999, 5, 1106;
37. f) D. V. Deubel, S. Schlecht, G. Frenking, J. Am. Chem. Soc. 2001, 123, 10085;
38. g) C. Zhou, D. M. Birney, J. Am. Chem. Soc. 2002, 124, 5231;
39. h) K. Kraft, G. Koltzenburg, Tetrahedron Lett. 1987, 28, 4357;
40. i) K. Kraft, G. Koltzenburg, Tetrahedron Lett. 1987, 28, 4723.
41. a) F. He, G. Cheng, H. Q. Zhang, Y. Zheng, Z. Q. Xie, B. Yang, Y. G. Ma, S. Y. Liu, J. C. Shen, Chem. Commun. 2003, 2206;
42. b) F. He, H. Xu, B. Yang, Y. Duan, L. L. Tian, K. K. Huang, Y. G. Ma, S. Y. Liu, S. H. Feng, J. C. Shen, Adv. Mater. 2005, 17, 2710;
43. c) F. He, L. L. Tian, X. Y. Tian, H. Xu, W. J. Xie, J. L. Xia, F. Z. Shen, B. Yang, F. Li, Y. G. Ma, Y. Q. Yang, J. C. Shen, Adv. Funct. Mater., in press.
44. a) S. Faure, S. Piva-Le-Blanc, C. Bertrand, J. P. Pete, R. Faure, O. Piva, J. Org. Chem. 2002, 67, 1061;
45. b) K. S. S. P. Rao, S. M. Hubig, J. N. Moorthy, J. K. Kochi, J. Org. Chem. 1999, 64, 8098;
46. c) S. Banerjee, S. Ghosh, J. Org. Chem. 2003, 68, 3981.
47. J. Liu, K. J. Boarman, Chem. Commun. 2005, 340.
48. L. P. Xu, C. J. Yan, L. J. Wan, S. G. Jiang, M. H. Liu, J. Phys. Chem. B 2005, 109, 14773.
49. K. Nakanishi, Infrared Absorption Spectroscopy - Practical, Holden-Day, San Francisco, 1962, pp. 24-27.
50. We are not considering a biradical mechanism at present because of the purity of the product and high stereospecificity of the reaction (hardly any side reaction occurred), as well as the mild conditions. The use of a radical initiator failed to trigger the reaction (see Supporting Information)..
51. R. A. Caldwell, J. Am. Chem. Soc. 1980, 102, 4004.
52. Through theoretical studies, we found that the meta substituents in DPA-TSB play an important role in decreasing the energy difference of the two energy minima and stabilizing the second stable conformation.
53. The predominant conformation adopted by an analogous molecule, 2,5,2′,5′-tetra(4-tert-butylphenyl)-1,1-biphenyl, as a result of a strong π-π interaction between the ortho-substituted arms is similar to the second stable conformation of DPA-TSB (with a dihedral angle of 116.6°); B. S. Nehls, F. Galbrecht, A. Bilge, D. J. Brauer, C. W. Lehmann, U. Scherf, T. Farrell, Org. Biomol. Chem. 2005, 3, 3213.
54. M. B. Smith, J. March, March's Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 5th ed., Wiley, New York, 2001, p. 1077.