Synthesis,structure, and transformation of 1-amino-5-phenyl- 2,6,6-tricyano-3-cyclopropyl-1, 3-cyclohexadiene into 6-phenyl-2-dicyanomethylene-3-cyano-4-cyclopropyl-1, 2-dihydropyridine |
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| Authors: | V N Nesterov V E Shklover Yu A Sharanin Yu T Struchkov G E Khoroshilov |
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| Institution: | (1) A. N. Nesmeyanov Institute of Organoelemental Compounds, Academy of Sciences of the USSR, Moscow;(2) T. G. Shevchenko Voroshilovgrad State Pedagogical Institute, USSR |
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| Abstract: | 1-Amino-5-phenyl-2,6,6-tricyano-3-cyclopropyl-1,3-cyclohexadiene is prepared by reaction of benzylidenemalononitrile with (1-cyclopropylethylidene) malononitrile. According to x-ray structural data, steric effects of the cyclohexadiene cause the C1-C6 and C5-C6 bond lengths to increase to 1.541(3) and 1.568(3) Å. The weakest bond of the cyclohexadiene, C5-C6, ruptures homolytically on external energy deposition with subsequent formation of a substituted dihydropyridine.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2776–2780, December, 1989. |
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