Electrophilic nitration of triphenylamines as a route to high oxidation potential electrocatalysts. Polynitration, nitrodebromination, and bromine dance

Tetrahedron Letters

Volumn 47, Issue 44, 2006, Pages 7667-7669

  Wu, Xin ^a   Dube, Mufaro A ^a   Fry, Albert J ^a  

^a WESLEYAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4,4',4'' TRIBROMOTRIPHENYLAMINE; ANILINE DERIVATIVE; BROMINE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CATALYSIS; ELECTROCHEMISTRY; NITRATION; OXIDATION; ROOM TEMPERATURE;

EID: 33748971001     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.139     Document Type: Article

References (16)

1. Kaimakliotis C., and Fry A.J. J. Org. Chem. 68 (2003) 9893
2. Schmidt W., and Steckhan E. Chem. Ber. 113 (1980) 577
3. Seo E.T., Nelson R.F., Fritsch J.M., Marcoux L.S., Leedy D.W., and Adams R.N. J. Am. Chem. Soc. 88 (1966) 3498
4. Mayers B.T., and Fry A.J. Org. Lett. 8 (2006) 411
5. 1H NMR spectroscopy and both low and high resolution mass spectrometries; see Supplementary data.
6. Nitration takes place at the 4-position of each ring, though 4-nitro compound 1c is accompanied by a trace (<1%) of the 2-isomer.
7. Saldabols N., Liepins E., and Popelis J. Zh. Org. Khim. 15 (1979) 2547
8. Hartshorn M.P., Robinson W.T., Vaughan J., and White J.M. Aust. J. Chem. 38 (1985) 575
9. Clewley R., Fischer A., and Henderson G.N. Can. J. Chem. 67 (1989) 1472
10. Arnold D.P., Bott R.C., Eldridge H., Elms F.M., Smith G., and Zojaji M. Aust. J. Chem. 50 (1997) 1997
11. Perrin C.L. J. Org. Chem. 36 (1971) 420
12. Olah G.A., Tolgyesi W.S., and Dear R.E.A. J. Org. Chem. 27 (1962) 3455
13. Olah G.A., Tolgyesi W.S., and Dear R.E.A. J. Org. Chem. 27 (1962) 3441
14. Augustijn G.J.P., Kooyman E.C., and Louw R. Recl. Trav. Chim. Pay-Bas 82 (1963) 965
15. Arzel E., Rocca P., Marsais F., Godard A., and Queguiner G. Heterocycles 50 (1999) 215
16. de Queiroz J.F., Carneiro J.W.d.M., Sabino A.A., Sparrapan R., Eberlin M.N., and Esteves P.M. J. Org. Chem. 71 (2006) 6192