Synthesis of Unexpected trans-meso Macrocycle from Novel Unsymmetrical Tetraphenylene

Synlett

Volumn 27, Issue 14, 2016, Pages 2095-2100

  Deng, Chun Lin ^a   Hau, Sam C K ^b   Peng, Xiao Shui ^a   Wong, Henry N C ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

cation interactions; host guest chemistry; macrocycle; nonplanar hydrocarbon; tetraphenylene

Indexed keywords

AROMATIC COMPOUND; CATION; CHEMICAL COMPOUND; MACROCYCLIC COMPOUND; ORGANIC COMPOUND; TETRAPHENYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTRON; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84976320009     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0035-1561480     Document Type: Article

References (49)

1. Rapson W. S., Shuttleworth R. G., Niekerk J. N. J. Chem. Soc.: 1943; 326
2. Irngartinger H., Reibel W. R. K. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem.: 1981; 37 1724
3. Mak T. C. W, Wong H. N. C. Top. Curr. Chem.: 1987; 140 141
4. Polycyclic Arenes and Heteroarenes: Synthesis, Properties and Applications. Miao Q. Wiley-VCH Weinheim: 2015
5. Peng H.-Y, Lam C. K., Mak T. C. W, Cai Z., Ma W.-T, Li Y.-X, Wong H. N. C. J. Am. Chem. Soc.: 2005; 127 9603
6. Lin F., Peng H. Y., Chen J. X., Chik D. T. W, Cai Z., Wong K. M. C, Yam V. W. W, Wong H. N. C. J. Am. Chem. Soc.: 2010; 132 16383
7. Chen J.-X, Han J.-W, Wong H. N. C. Org. Lett.: 2015; 17 4296
8. Huang H., Hau C.-K, Law C. C. M, Wong H. N. C. Org. Biomol. Chem.: 2009; 7 1249
9. Hau C.-K, He H., Lee A. W. M, Chik D. T. W, Cai Z., Wong H. N. C. Tetrahedron: 2010; 66 9680
10. Lim D. S. W, Anderson E. A. Synthesis: 2012; 44 983
11. Wen J.-F, Hong W., Yuan K., Mak T. C. W, Wong H. N. C. J. Org. Chem.: 2003; 68 8918
12. Cui J.-F, Chen C., Gao X., Cai Z., Han J.-W, Wong H. N. C. Helv. Chim. Acta: 2012; 95 2604
13. Sygula A., Fronczek F. R., Sygula R., Rabideau P. W., Olmstead M. M. J. Am. Chem. Soc.: 2007; 129 3842
14. Deng C.-L, Xiong X.-D, Chik D. T. W, Cai Z., Peng X.-S, Wong H. N. C. Chem. Asian J.: 2015; 10 2342
15. Rathore R., Magueres P. L., Lindeman S. V., Kochi J. K. Angew. Chem. Int. Ed.: 2000; 39 809
16. Ogasawara J., Igarashi T., Sano S. US 20050112407: 2005
17. Wuckert E., Hägele C., Giesselmann F., Baro A., Laschat S. Beilstein J. Org. Chem.: 2009; 5 57
18. Hägele C., Wuckert E., Laschat S., Giesselmann F. ChemPhysChem: 2009; 10 1291
19. Hau C. K., Chui S. S. Y, Lu W., Che C. M., Cheng P. S., Mark T. C. M, Miao Q., Wong H. N. C. Chem. Sci.: 2011; 2 1068
20. Nielsen C., Brock-Nannestad T., Reenberg T., Hammershoj P., Christensen J., Stouwdam J., Pittelkow M. Chem. Eur. J.: 2010; 16 13030
21. Brotin T., Dutasta J.-P. Chem. Rev.: 2009; 109 88
22. Hardie M. J. Chem. Soc. Rev.: 2010; 39 516
23. Chatelet B., Joucla L., Padula D., Di Bari L., Pilet G., Robert V., Dufaud V., Dutasta J.-P, Martinez A. Org. Lett.: 2015; 17 500
24. Schmitt A., Robert V., Dutasta J.-P, Martinez A. Org. Lett.: 2014; 16 237
25. Li M.-J, Huang C.-H, Lai C.-C, Chiu S.-H. Org. Lett.: 2012; 14 6146
26. Wang L., Wang G.-T, Zhao X., Jiang X.-K, Li Z.-T. J. Org. Chem.: 2011; 76 3531
27. Canevet D., Gallego M., Isla H., de Juan A., Pérez E. M., Martín N. J. Am. Chem. Soc.: 2011; 133 3184
28. Markopoulos G., Henneicke L., Shen J., Okamoto Y., Jones P. G., Hopf H. Angew. Chem. Int. Ed.: 2012; 51 12884
29. Kuck D. Chem. Rev.: 2006; 106 4885
30. Bredenkötter B., Grzywa M., Alaghemandi M., Schmid R., Herrebout W., Bultinck P., Volkmer D. Chem. Eur. J.: 2014; 20 9100
31. Klotzbach S., Beuerle F. Angew. Chem. Int. Ed.: 2015; 54 10356
32. Wei J., Li Z.-M, Jin X.-J, Yao X.-J, Cao X.-P, Chow H.-F, Kuck D. Chem. Asian J.: 2015; 10 1150
33. Wang T., Zhang Y.-F, Hou Q.-Q, Xu W.-R, Cao X.-P, Chow H.-F, Kuck D. J. Org. Chem.: 2013; 78 1062
34. Klotzbach S., Scherpf T., Beuerle F. Chem. Commun.: 2014; 50 12454
35. Xu W.-R, Xia G.-J, Chow H.-F, Cao X.-P, Kuck D. Chem. Eur. J.: 2015; 21 12011
36. Chen C.-F. Chem. Commun.: 2011; 47 1674
37. Ma Y.-X, Han Y., Chen C.-F. J. Incl. Phenom. Macrocycl. Chem.: 2014; 79 261
38. Chen C.-F, Ma Y.-X. Iptycenes Chemistry: From Synthesis to Applications. Springer Heidelberg: 2013
39. Han Y., Meng Z., Ma Y.-X, Chen C.-F. Acc. Chem. Res.: 2014; 47 2026
40. Mastalerz M. Synlett: 2013; 24 781
41. Chong J. H., MacLachlan M. J. Chem. Soc. Rev.: 2009; 38 3301
42. Keyworth C. W., Chan K. L., Labram J. G., Anthopoulos T. D., Watkins S. E., MaKiernan M., White A. J. P, Holmes A. B., Williams C. K. J. Mater. Chem.: 2011; 21 11800
43. Collibee S. E., Yu J. Tetrahedron Lett.: 2005; 46 4453
44. Pialat A., Liégault B., Taillefer M. Org. Lett.: 2013; 15 1764
45. Daze K. D., Hof F. Acc. Chem. Res.: 2013; 46 937
46. Ma J. C., Dougherty D. A. Chem. Rev.: 1997; 97 1303
47. Salonen L. M., Ellermann M., Diederich F. Angew. Chem. Int. Ed.: 2011; 50 4808
48. Pena P. V., Davrazou F., Shi X. B., Walter K. L., Verkhusha V. V., Gozani O., Zhao R., Kutateladze T. G. Nature (London, U.K.): 2006; 442 100
49. Mahadevi A. S., Sastry G. N. Chem. Rev.: 2013; 113 2100