Abstract
2,5-Dimethyl- and 2-ethyl-5-methyl-1,3-benzodithiolium perchlorates react with dimethylformamide and N-phenyl-N-methylaminoacrolein to give monoiminium salts, the hydrolysis of which yields the corresponding aldehydes. The trans-transoid structure ofβ-formylvinyl-substituted 2-methylenebenzo-1,3-dithioles was established by a comparison of the experimental and calculated dipole moments, absorption maxima, and intensities of the electron transitions and also by analysis of the PMR spectra.
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N. E. Shelepin, N. S. Loseva, L. E. Nivorozhkin, and V. I. Minkin, Khim. Geterotsikl. Soedin., 733 (1971).
G. A. Reynold and G. A. Wan Allan, J. Org. Chem.,34, 2736 (1969).
L. A. Janovskaya, G. V. Kryshtal, V. F. Kucherov, B. Y. Simkin, B. A. Bren' (Bren), and V. I. Minkin, Tetrahedron,29, 2053 (1973).
R. G. Parr, The Quantum Theory of Molecular Electronic Structure, New York (1964).
V. G. Dashevskii and I. O. Murtazina, Scientific Results [in Russian], Khimiya, Nauka (1969), p. 6.
G. Hedestrand, Z. Phys. Chem.,B2, 428 (1929).
V. I. Minkin, B. Y. Simkin, and L. P. Olechnovich, Int. J. Sulfur Chem.,3A, 249 (1973).
W. F. Cooper, N. C. Kenny, and J. W. Edmonds, Chem. Commun., 889 (1971).
L. E. Orgel, F. L. Sutton, F. L. Cottrell, and W. Dick. Trans. Faraday Soc.,47, 113 (1951).
L. Soder and R. Wizinger, Helv. Chim. Acta,42, 1733 (1959).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1485–1488, November, 1974.
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Loseva, N.S., Nivorozhkin, L.E., Borisenko, N.I. et al. Formyl and formylvinyl derivatives of 2-methylenebenzo-1,3-dithiole. Chem Heterocycl Compd 10, 1305–1308 (1974). https://doi.org/10.1007/BF01175084
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DOI: https://doi.org/10.1007/BF01175084