Abstract
The reaction between the cyanoacridinium cation and sodium borohydride was studied by EPR spectroscopy and cyclical voltammetry. It is shown that the formation of a cyanoacridinyl radical precedes the formation of the reaction product, viz., N-methyl-9-cyano-9,10-dihydroacridine. It is concluded that the borohydride anion may be an electron-donor in this reaction.
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Literature cited
A. Hajos, Complex Hydrides in Organic Chemistry [Russian translation], Khimiya, Moscow (1971), p. 24.
V. Gerard, The Chemistry of Organic Compounds [Russian translation], Khimiya, Moscow (1966), p. 159.
E. C. Ashby and A. B. Goel, Tetrahedron Lett., 22, 4783 (1982).
E. C. Ashby and A. B. Goel, Tetrahedron Lett., 22, 1879 (1981).
E. C. Ashby, A. B. Goel, and R. N. de Priest, Tetrahedron Lett., 22, 4355 (1981).
E. C. Ashby and A. B. Goel, Tetrahedron Lett., 22, 3729 (1981).
P. R. Singh and A. Nigam, Tetrahedron Lett., 21, 4753 (1980).
P. R. Singh, J. M. Khurama, and A. Nigam, Tetrahedron Lett., 22, 2901 (1981).
A. S. Morkovnik, O. Yu. Okhlobystin, and N. M. Dobaeva, Khim. Geterotsikl. Soedin., No. 10, 1428 (1979).
O. N. Chupakhin, I. M. Sosonkin, and A. I. Matern, Dokl. Akad. Nauk SSSR, 250, 875 (1980).
J. W. Happ and E. G. Janzen, J. Org. Chem., 35, 96 (1970).
J. W. Happ and E. G. Janzen, J. Org. Chem., 35, 3224 (1970).
I. M. Sosonkin, O. N. Chupakhin, and A. I. Matern, Zh. Org. Khim., 15, 1976 (1979).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1377–1379, October, 1983.
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Sosonkin, I.M., Matern, A.I. & Chupakhin, O.N. Electron transfer in the reduction of the acridinium cation with borohydride. Chem Heterocycl Compd 19, 1097–1099 (1983). https://doi.org/10.1007/BF00505764
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DOI: https://doi.org/10.1007/BF00505764