Abstract
Reaction of chloranil with excess pyridine gives the poorly stable 2,5-di(N-pyridinium)-3,6-dichloro-1,4-benzoquinone dichloride which is readily hydrolyzed to give the bisbetaine of 2,5-di(N-pyridinium)-1,4-benzoquinone-3,6-dioxide. Treatment with acid gives its mono- and bisprotonated derivatives as the perchlorate and dibromide and bromination gives the betaine 2-bromo-2,5-di(N-pyridinium)-5-cyclohexene-1,3,4-trione-6-oxide perbromide. The reaction of malonodinitrile with 2,5-di(N-pyridinium)-3,6-dichloro-1,4-benzoquinone dichloride in situ gives the poorly stable bisbetaine of 2,5-di(N-pyridinium)-7,7,8,8-tetracyanoquinodimethane-3,6-dioxide.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
K. Th. Finley, in: The Chemistry of the Quinonoid Compounds, S. Patai (ed.), Vol. 1, Part 2, John Wiley (1974), p. 877.
K. Th. Finley, in: The Chemistry of the Quinonoid Compounds, S. Patai and Z. Rappoport (eds.), Vol. 2, Part 1, John Wiley, Chichester (1988), p. 719.
A Schönberg and A. F. A. Ismail, J. Chem. Soc., 1374 (1940).
H. D. Baernstein, J. Am. Chem. Soc.,67, 1437 (1945).
J. A. Van Allan and G. A. Reynolds, J. Org. Chem.,28, 1019 (1963).
J. A. Van Allan and G. A. Reynolds, J. Org. Chem.,28, 1022 (1963).
G. A. Reynolds, R. E. Adel, and J. A. Van Allan, J. Org. Chem.,28, 2683 (1963).
J. A. Van Allan, G. A. Reynolds, and R. E. Adel, J. Org. Chem.,28, 3502 (1963).
R. Weiss, N. J. Salomon, G. E. Miess, and R. Roth, Angew. Chem. Int. Ed. (in Engl.),25, 917 (1986).
S. Iwatsuki, M. Kubo, and H. Iwase, Chem. Lett., 517 (1993).
O. Ya. Neiland, Izv. Akad. Nauk Latv. SSR., Ser. Fiz. Tekhn., Nauk, No. 6, 63 (1981).
C. Vazquez, J. C. Calabrese, D. A. Dixon, and J. S. Miller, J. Org. Chem.,58, 65 (1993).
S. Berger and A. Rieker, in: The Chemistry of the Quinonoid Compounds, S. Patai (ed.), Vol. 1, Part 1, John Wiley (1974), p. 163.
E. Pretsch, Th. Clerc, J. Seibl, and W. Simon, Tables of Spectral Data for Structure Determinations of Organic Compounds, 2nd Ed., Springer-Verlag, Berlin (1989).
S. P. Valter, Structure and Tautomeric Conversions of β-Dicarbonyl Compounds, Zinatne, Riga (1977), p. 142.
M. L. Jain, R. P. Soni, and J. P. Saxena, Indian J. Chem.,19B, 718 (1980).
L. R. Melby, R. J. Harder, W. R. Hertler, W. Mahler, R. E. Benson, and W. E. Mochel, J. Am. Chem. Soc.,84, 3374 (1962).
A. S. Koch, W. G. Harbison, J. M. Hubbard, M. de Kort, and B. A. Roe, J. Org. Chem.,61, 5959 (1996).
I. Heilbron and G. M. Bunbury (eds.), Dictionary of Organic Compounds [Russian translation], Vol. 1, Inostr. Lit., Moscow (1949), p. 309.
Additional information
Riga Technical University, Riga LV-1048. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 346–349, March, 1998.
Rights and permissions
About this article
Cite this article
Yanchishin, V.A., Karlivan, G.A. & Valter, R.É. Synthesis and properties of dipyridinium betaines of derivatives of 1,4-benzoquinone and tetracyanoquinodimethane. Chem Heterocycl Compd 34, 312–315 (1998). https://doi.org/10.1007/BF02290722
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02290722