Synthesis of Polyfunctional Aromatic Imines with Zwitterionic Character

Abstract

Polyfunctional aromatic imines with a zwitterionic character involving sulfonic acid and N,N-dimethylamino functionalities are synthesized by oxidative condensation of 5-aminonaphthalene-2-sulfonic acid (Cleve's β-acid) and N,N-dimethyl-p-phenylenediamine.

References

1. H. McConnell, J. Chem. Phys., 1963, 39, 1910.
2. (a) M. Tamura, Y. Nakazawa, D. Shiomi, K. Nozawa, Y. Hosokoshi, M. Ishikawa, M. Takahashi and M. Kinoshita, Chem. Phys. Lett., 1991, 186, 5, 401; (b) A. Rassat and R. Chiarelli, Magn. Mol. Mater., 1991, 191; (c) Y. Hosokoshi, M. Tamura, M. Kinoshita, H. Sawa, R. Kato and Y. Fujiwara, J. Mater. Chem., 1994, 4, 1219; (d) K. Inoue and H. Iwamura, Mol. Cryst. Liq. Cryst., 1993, 232, 89; (e) K. Awaga, T. Inabe, Y. Maruyama, T. Nakamura and M. Matsumoto, Chem. Phys. Lett., 1992, 195, 21; (f) K. Awaga, A. Yamaguchi, T. Okuno, T. Inabe, T. Nakamura, M. Matsumoto and Y. Maruyama, J. Mater. Chem., 1994, 4, 1377; (g) T. Sugano, M. Tamura, M. Kinoshita, Y. Sakai and Y. Ohashi, Chem. Phys. Lett., 1992, 200, 235.
3. (a) T. Sugawara, S. Bandow, K. Kimura, H. Iwamura and K. Itoh, J. Am. Chem. Soc., 1986, 108, 368; (b) S. K. Silverman and D. A. Dougherty, J. Phys. Chem., 1993, 97, 13273.
4. (a) S. Galaj, A. Le Méhauté, F. Tsobnang, D. Cottevieille, A. Léaustic, R. Clément, V. Cagan, M. Guyot, J. C. Fayet, B. Villeret, L. Noirez and A. Périchaud, J. Magn. Magn. Mater., 1995, 140–144, 1445; (b) A. Le Méhauté, F. Tsobnang, M. R. Soriano, S. Galaj, D. Cottevieille, A. Léaustic, R. Clément, V. Cagan, M. Guyot, E. Geniès, J. C. Fayet and B. Villeret, J. Chim. Phys., 1995, 92, 971.
5. Y. Wei, C. Jang and T. Ding, Tetrahedron Lett., 1996, 37, 731.