Practical and efficient synthesis of tris(4-formylphenyl)amine, a key building block in materials chemistry

Synthesis

Volumn , Issue 11, 2005, Pages 1771-1774

  Mallegol, Thomas ^a   Gmouh, Said ^a   Meziane, Mohamed Aït Amer ^a   Blanchard Desce, Mireille ^a   Mongin, Olivier ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Aldehydes; Building block; Electrophilic aromatic substitutions; Materials chemistry; Vilsmeier Haack reaction

Indexed keywords

AMINES; HYDROLYSIS; SUBSTITUTION REACTIONS;

BIS-IMINIUM INTERMEDIATES; MATERIAL CHEMISTRY; TRIPHENYLAMINE; TWO-FLASK SYNTHESIS;

SYNTHESIS (CHEMICAL);

ALDEHYDE; BENZENE DERIVATIVE; TRIS(4 FORMYLPHENYL)AMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; VILSMEIER HAACK REACTION;

EID: 23044467732     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865336     Document Type: Article

References (26)

1. Suzuki, H.; Matsumoto, M. Jpn. Kokai Tokkyo Koho, 63163361, 1988.
2. Goto, S.; Abe, N.; Sasaki, O. Jpn. Kokai Tokkyo Koho, 01044452, 1989.
3. Kushibiki, N.; Takeuchi, K.; Kobayashi, H.; Masatomi, T. Eur. Pat. Appl., 771809, 1997.
4. Nam, H.; Kang, D. H.; Kim, J. K.; Park, S. Y. Chem. Lett. 2000, 1298.
5. Jiang, K. J.; Sun, Y. L.; Shao, K. F.; Yang, L. M. Chem. Lett. 2004, 33, 50.
6. Meng, F. S.; Yao, Q. H.; Shen, J. G.; Li, F. L.; Huang, C. H.; Chen, K. C.; Tian, H. Synth. Met. 2003, 137, 1543.
7. Meng, F.; Liu, C.; Hua, J.; Cao, Y.; Chen, K.; Tian, H. Eur. Polym. J. 2003, 39, 1325.
8. Elandaloussi, E. H.; Spangler, C. W. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1998, 39, 1055.
9. Holmberg, S. E.; Spangler, C. W. Polym. Mater. Sci. Eng. 2001, 54, 717.
10. Stadler, S.; Feiner, F.; Bräuchle, C.; Brandl, S.; Gompper, R. Chem. Phys. Lett. 1995, 245, 292.
11. Lambert, C.; Gaschler, W.; Schmalzlin, E.; Meerholz, K.; Brauchle, C. J. Chem. Soc., Perkin Trans. 2 1999, 577.
12. Elandaloussi, E. H.; Spangler, C. W.; Dirk, C.; Casstevens, M.; Kumar, D.; Burzynski, R. Mater. Res. Soc. Symp. Proc. 1999, 561, 63.
13. Drobizhev, M.; Karotki, A.; Rebane, A.; Spangler, C. W. Opt. Lett. 2001, 26, 1081.
14. Yoo, J.; Yang, S. K.; Jeong, M.-Y.; Ahn, H. C.; Jeon, S.-J.; Cho, B. R. Org. Lett. 2003, 5, 645.
15. Drobizhev, M.; Karotki, A.; Dzenis, Y.; Rebane, A.; Suo, Z.; Spangler, C. W. J. Phys. Chem. B 2003, 107, 7540.
16. Spangler, C. W.; Suo, Z.; Drobizhev, M.; Karotki, A.; Rebane, A. Proc. SPIE-Int. Soc. Opt. Eng. 2003, 4797, 146.
17. Spangler, C. W.; Suo, Z.; Drobizhev, M.; Karotki, A.; Rebane, A. NATO Sci. Ser. II 2003, 100, 139.
18. Mongin, O.; Porrès, L.; Katan, C.; Pons, T.; Mertz, J.; Blanchard-Desce, M. Tetrahedron Lett. 2003, 44, 8121.
19. Lee, H. J.; Sohn, J.; Hwang, J.; Park, S. Y.; Choi, H.; Cha, M. Chem. Mater. 2004, 16, 456.
20. Yang, W. J.; Kim, D. Y.; Kim, C. H.; Jeong, M.-Y.; Lee, S. K.; Jeon, S.-J.; Cho, B. R. Org. Lett. 2004, 6, 1389.
21. Mongin, O.; Charlot, M.; Katan, C.; Porrès, L.; Parent, M.; Pons, T.; Mertz, J.; Blanchard-Desce, M. Proc. SPIE-Int. Soc. Opt. Eng. 2004, 5516, 9.
22. Hua, J. L.; Li, B.; Meng, F. S.; Ding, F.; Qian, S. X.; Tian, H. Polymer 2004, 45, 7143.
23. Wilson, C. D. US Patent, 2558285, 1951.
24. Lai, G.; Bu, X. R.; Santos, J.; Mintz, E. A. Synlett 1997, 1275.
25. 3. To overcome this problem, other authors tried to use high boiling chlorinated solvents, such as 1,2-dichloroethane, but the yields remained low.
26. Jin, S.-H.; Jung, J.-E.; Yeom, I.-S.; Moon, S.-B.; Koh, K.; Kim, S.-H.; Gal, Y.-S. Eur. Polym. J. 2002, 38, 895.