Abstract
4,5,4′,5′-Tetrakis(dimethylamino)-1,1′-binaphthalene, unknown previously, was obtained in ∼20% yield by the oxidation of 1,8-bis(dimethylamino)naphthalene with Tl(OAc)3 or Pb(OAc)4 at low temperatures. Treatment of the reaction product with excess Li and then with O2 gave, depending on the reaction temperature, perylene or 4,4′-bis(dimethylamino)-1,1′-binaphthalene in good yields, instead of expected 3,4,9,10-tetrakis(dimethyl-amino)perylene.
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A. F. Pozharskii and V. A. Ozeryanskii,Izv. Akad. Nauk, Ser. Khim., 1998, 68 [Russ. Chem. Bull., 1998,47, 66 (Engl. Transl.)].
N. V. Vistorobskii, O. V. Vinogradova, and A. F. Pozharskii,Izv. Akad. Nauk, Ser. Khim., 1997, 348 [Russ. Chem. Bull., 1997,46, 334 (Engl. Transl.)].
A. F. Pozharskii, A. N. Suslov, N. M. Starshikov, L. L. Popova, N. A. Klyuev, and V. A. Adanin,Zh. Org. Khim., 1980,16, 2216 [J. Org. Chem. USSR, 1980,16 (Engl. Transl.)].
J. P. Maier,Helv. Chim. Acta, 1974,57, 994.
N. T. Berberova and O. Yu. Okhlobystin,Zh. Org. Khim., 1983,19, 1114 [J. Org. Chem. USSR, 1983,19 (Engl. Transl.)].
K. Ding, Y. Wang, L. Zhang, and Y. Wu,Tetrahedron, 1996,52, 1005.
A. McKillop, A. G. Turell, and E. C. Taylor,J. Org. Chem., 1977,42, 764; A. McKillop, A. G. Turrell, D. W. Young, and E. C. Taylor,J. Am. Chem. Soc., 1980,102, 6504.
K. A. Kerr and J. M. Robertson,J. Chem. Soc. (B), 1969, 1146.
R. W. Alder and J. E. Anderson,J. Chem. Soc., Perkin Trans. 2, 1973, 2086.
H. Einspahr, J. -B. Robert, R. E. Marsh, and J. Roberts,Acta Crystallogr B, 1973,29, 1611.
K. Wozniak, H. He, J. Klinowski, and E. Grech,J. Phys. Chem., 1995,99, 1403.
Z. Dega-Szafran, B. Niwak-Wydra, and M. Szafran,Magn. Res. Chem., 1993,31, 726.
G. Dyker,J. Org. Chem., 1993,58, 234.
N. V. Vistorobskii and A. F. Pozharskii,Zh. Org. Khim., 1996,32, 71 [Russ. J. Org. Chem., 1996,32 (Engl. Transl.)].
P. Michel and A. Moradpour,Synthesis, 1988, 894.
F. Gerson, E. Haselbach, and G. Plattner,Chem. Phys. Lett., 1971,12, 316.
M. C. Miras, J. J. Silberg, and L. Sereno,J. Electroanal. Chem., 1986,201, 367.
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For Part 23, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 93–98, January, 1998.
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Vistorobskii, N.V., Pozharskii, A.F. & Rudnev, M.I. peri-Naphthylenediamines. Russ Chem Bull 47, 91–96 (1998). https://doi.org/10.1007/BF02495514
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DOI: https://doi.org/10.1007/BF02495514