Two-step synthesis of hexaammonium triptycene: An air-stable building block for condensation reactions to extended triptycene derivatives

Journal of Organic Chemistry

Volumn 76, Issue 15, 2011, Pages 6389-6393

  Mastalerz, Michael ^a   Sieste, Stefanie ^a   Cenić, Mila ^a   Oppel, Iris M ^b  

^a UNIVERSITY OF ULM   (Germany)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AIR-STABLE; BENZIMIDAZOLES; BENZOTRIAZOLES; BUILDING BLOCKES; HIGH YIELD; QUINOXALINES; TRIPTYCENES; TWO-STEP SYNTHESIS;

CONDENSATION;

CONDENSATION REACTIONS;

2,3,6,7,12,13 HEXA(40 METHOXYPHENYL) 2,6,12 TRIHYDROTRIPTY [2,3 D:6,7 D':12,13 D'']TRIPYRAZYL; 2,3,6,7,12,13 HEXAHYDROXY 2,6,12 TRIHYDROTRIPTY[2,3 D:6,7 D':12,13 D'']TRIPYRAZYL; 2,3,6,7,14,15 HEXAAMMONIUMTRIPTYCENE HEXACHLORIDE; 2,3,6,7,14,15 HEXANITROTRIPTYCENE; 2,6,12 TRIHYDROTRIPTY[2,3 D:6,7 D':12,13 D'']TRIAZOLE; 2,6,12 TRIHYDROTRIPTY[2,3 D:6,7 D':12,13 D'']TRIPYRAZYL; 2,6,12 TRIHYDROTRIPTY[2,3 D:6,7 D':12,13 D']TRIIMIDAZOLE; BENZIMIDAZOLE; BENZOTRIAZOLE DERIVATIVE; HEXAAMMONIUM TRIPTYCENE; QUINOXALINE DERIVATIVE; TRIPTYCENE DERIVATIVE; TRIS NICKELSALPHEN; UNCLASSIFIED DRUG;

AIR; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL PARAMETERS; MOLECULAR STABILITY; POLYMERIZATION; SYNTHESIS;

EID: 79961078501     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200843v     Document Type: Article

References (33)

1. Bartlett, P. D.; Ryan, M. J.; Cohen, S. G. J. Am. Chem. Soc. 1942, 64, 2649-2653
2. Chong, J. H.; MacLachlan, M. J. Chem. Soc. Rev. 2009, 38, 3301-3315
3. Zhao, L.; Li, Z.; Wirth, T. Chem. Lett. 2010, 39, 658-668
4. Harada, N.; Uda, H. J. Chem. Soc., Perkin Trans. 2 1989, 1449-1453
5. Yang, J.-S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 5321-5322
6. Zhao, D.; Swager, T. M. Org. Lett. 2005, 7, 4357-4360
7. Zhu, Z.; Swager, T. M. Org. Lett. 2001, 3, 3471-3474
8. Long, T. M.; Swager, T. M. J. Am. Chem. Soc. 2003, 125, 14113-14119
9. Perepichka, D. F.; Bendikov, M.; Meng, H.; Wudl, F. J. Am. Chem. Soc. 2003, 125, 10190-10191
10. Kelly, T. R.; Cai, X.; Damkaci, F.; Panicker, S. B.; Tu, B.; Bushell, S. M.; Cornella, I.; Pigott, M. J.; Salives, R.; Cavero, M.; Zhao, Y.; Jasmin, S. J. Am. Chem. Soc. 2007, 129, 376-386
11. See, for instance: Zhou, X.-Z.; Chen, C.-F. J. Am. Chem. Soc. 2005, 127, 13158-13159
12. For a review covering macrocycles based on triptycenes, see: Chen, C.-F. Chem. Commun. 2011, 47, 1674-1688
13. Mastalerz, M. Chem. Commun. 2008, 4756-4758
14. Mastalerz, M.; Schneider, M. W.; Oppel, I. M.; Presly, O. Angew. Chem., Int. Ed. 2011, 50, 1046-1051
15. Chong, J. H.; MacLachlan, M. J. Inorg. Chem. 2006, 45, 1442-1444
16. Vagin, S.; Ott, A.; Weiss, H.-C.; Karbach, A.; Volkmer, D.; Rieger, B. Eur. J. Inorg. Chem. 2008, 2601-2609
17. Vagin, S. I.; Ott, A. K.; Hofmann, S. D.; Lanziger, D.; Rieger, B. Chem.-Eur. J. 2009, 15, 5845-5853
18. Ghanem, B. S.; Msayib, K. J.; McKeown, N. B.; Harris, K. D. M.; Pan, Z.; Budd, P. M.; Butler, A.; Selbie, J.; Book, D.; Walton, A. Chem. Commun. 2007, 67-68
19. Ghanem, B. S.; Hashem, M.; Harris, K. D. M.; Msayib, K. J.; Xu, M. C.; Budd, P. M.; Chaukura, N.; Book, D.; Tedds, S.; Walton, A.; McKeown, N. B. Macromolecules 2010, 43, 5287-5294
20. For reviews, see: Wezenberg, S. J.; Kleij, A. W. Angew. Chem., Int. Ed. 2008, 47, 2354-2364
21. Kleij, A. W. Chem.-Eur. J. 2008, 14, 10520-10529
22. For a review on N -hetarenes, including quinoxalines, see: Bunz, U. H. F. Chem.-Eur. J. 2009, 15, 6780-6789
23. Preston, P. N. Chem. Rev. 1974, 74, 279-314
24. Chong, J. H.; MacLachlan, M. J. J. Org. Chem. 2007, 72, 8683-8690
25. Jiang, Y.; Chen, C.-F. Synlett 2010, 11, 1679-1681
26. Chong, J. H.; Ardakani, S. J.; Smith, K. J.; MacLachlan, M. J. Chem.-Eur. J. 2009, 15, 11824-11828
27. Shalaev, V. K.; Getmanova, E. V.; Skvarchenko, V. R. Zh. Org. Khim. 1976, 12, 191-197
28. A similar octaammonium chloride salt derivative of a cavitand was synthesized in a similar fashion: Far, A. R.; Shivanyuk, A.; Rebek, J., Jr. J. Am. Chem. Soc. 2002, 124, 2854-2855
29. The synthesis of hexanitrotriptycene 3 from further nitration of a regioisomeric mixture of trinitrotriptycenes on small scale was previous described by: Shalaev, V. K.; Skvarchenko, V. R. Vestn. Mosk. Univ. Ser. 2:Khim 1974, 15, 726-730
30. Damshoder, R. E.; Peterson, W. D. Org. Synth. 1940, 20, 16-18
31. Tellenbröcker, J.; Kuck, D. Angew. Chem., Int. Ed. 1999, 111, 919-922
32. For a review of centropolyindanes, see: Kuck, D. Chem. Rev. 2006, 106, 4885-4925
33. Sheldrick, G. M. SHELXTL-97, Universität Göttingen, Göttingen, Germany, 1997.