Abstract
Dispiro[bis(3-aminoindene)-1′,4;1′,5-(1,3-dithiolanes)] react readily with Cu+, Ag+, Hg+, and Hg2+ salts to give the corresponding bis(1-imino-3-indenyls) and methanedithiol derivatives. Bis(1-oxo-3-indenyls) are formed when the reaction is carried out in the presence of water. The reactivities of the 1,3-dithiolanes were examined with allowance for electronic and steric factors, and the reactivities of the metal cations were examined from the point of view of Pearson's theory. Methods for the alternative synthesis of the compounds obtained were found, and their IR and PMR spectra are discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
L. V. Timokhina, Ya. S. Tsetlin, E. O. Tsetlina, V. A. Usov, and M. G. Voronkov, Zh. Org. Khim., 15, 82 (1979).
E. Bergmann, M. Magat, and D. Wagenberg, Ber., 63, 2576 (1930).
A. Schonberg, B. Konig, and E. Singer, Ber., 100, 767 (1967).
A. Schonberg and S. Nickel, Ber., 64, 2323 (1931).
A. Schonberg, M. Elkaschef, M. Nosseir, and M. Sidky, J. Amer. Chem. Soc., 80, 6312 (1958).
F. Sondheimer and S. Wolfe, Can. J. Chem., 37, 1870 (1959).
L. Fieser and M. Fieser, Reagents for Organic Synthesis, Vol. 3, Wiley.
N. A. Korchevin, V. A. Usov, E. O. Tsetlina, V. A. Pestunovich, and M. G. Voronkov, Khim. Geterotsikl. Soedin., No. 1, 36 (1978).
Ya. F. Freimanis, The Chemistry of Enamino Ketones, Enamino Imines, and Enamino Thiones [in Russian], Zinatne, Riga (1974), p. 224.
Tse-Lok Ho, Chem. Rev., 75, 1 (1975).
J. F. W. McOmie, (editor), Protective Groups in Organic Chemistry [Russian translation], Mir, Moscow (1976), p. 248.
K. Lehmstedt and H. Haudertmark, Ber., 63, 1229 (1930).
N. A. Korchevin, V. A. Usov, and M. G. Voronkov, Khim. Geterotsikl. Soedin., No. 5, 713 (1974).
B. J. Whitlock and H. W. Whitlock, J. Org. Chem., 37, 3559 (1972).
C. A. Buehler and D. E. Pearson, Survey of Organic Syntheses, Wiley, New York (1970).
L. Fieser and M. Fieser, Reagents for Organic Synthesis, Vol. 1, Wiley.
Author information
Authors and Affiliations
Additional information
Communication 10 from the series “α,Β-Unsaturated Thio Compounds.” See [1] for communication 9.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 329–333, March, 1979.
Rights and permissions
About this article
Cite this article
Korchevin, N.A., Usov, V.A., Tsetlina, E.O. et al. Cleavage of substituted dispiro [bis(3′-aminoindene)-1′, 4;1′,5-(1,3-dithiolanes)] by means of transition metal salts. Chem Heterocycl Compd 15, 269–273 (1979). https://doi.org/10.1007/BF00474089
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00474089