Abstract
To select a method for the synthesis of the previously difficulty accessible 5-bromo-1-phenyl-1,2,4-triazole (I) and 1-phenyl-1,2,4-triazoline-5-thione (II), a MO LCAO calculation has been carried out in Huckel's approximation of the energies of the radical, electrophilic, and nucleophilic localization on the various carbon atoms of 1-phenyl-1,2,4-triazole (III). In accordance with this calculation, the required compounds have been obtained in good yields by reactions taking place by a radical mechanism: I by bromination with bromosuccinimide and II by the direct thionation of III. The high reactivity of the bromine atom in position 5 has been noted.
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References
I. Ya. Postovskii and I. L. Shegal, KhGS [Chemistry of Heterocyclic Compounds], 2, 443, 1966.
B. Pullman and A. Pullman, Quantum Biochemistry [Russian translation], IL, Moscow, p. 92, 1965.
B. Pullman, Rev. Mod. Phys., 32, 428, 1960.
B. Chubar, Mechanisms of Organic Reactions [Russian translation], IL, Moscow, p. 116, 1963.
L. Rolla, Gazz. Chim. Ital., 38, 348, 1908.
M. Pesson, S. Dupin, and G. Polmans, Bull. Soc. Chim. France, 1581, 1961.
N. V. Koshkin, Tr. Leningr. tekhnol. inst. pishchev. prom., 15, 91, 1958; C. A. 53, 19676, 1959.
G. Pellizzari and A. A. Ferro, Gazz. Chim. Ital., 28, 555, 1898.
Minoru Sekiya and Shizuma Ishikawa, Yakugaku Zasshi, 78, 549, 1958; C. A., 52, 17244, 1958.
L. Rolla, Gazz. Chim. Ital., 38, 343, 1908.
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For part VIII, see [1].
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Kovalev, E.G., Postovskii, I.Y. Investigations in the 1,2,4-triazole series. Chem Heterocycl Compd 4, 544–545 (1971). https://doi.org/10.1007/BF00486784
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DOI: https://doi.org/10.1007/BF00486784