Conclusions
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1.
Condensation of 1,1,2,2-tetracyanoethane with crotonaldehyde and the solvent (alcoholic medium) takes place in the ratio 1∶2∶1 to give 2-amino-5-methyl-3-(1-methyl-3-alkoxyallyl)-1-formyl-3, 4,4-tricyanoyclopentenes.
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2.
On the basis of an x-ray diffraction analysis of the product with an isopropoxy-group in the 3-position, the main features of its molecular structure are discussed, and a stepwise route is proposed for the reaction and its stereochemical features examined.
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Literature cited
A. B. Zolotoi, S. V. Konovalikhin, P. M. Lukin, et al., Khim. Geterotsikl. Soedin., 1238 (1988).
S. P. Zil'berg, O. E. Nasakin, P. M. Lukin, et al., Zh. Org. Khim.,24, 1014 (1988).
O. E. Nasakin, P. M. Lukin, S. P. Zil'berg, et al., Zh. Org. Khim.,24, 997 (1988).
O. E. Nasakin, P. M. Lukin, S. P. Zil'berg, et al., Zh. Org. Khim.,24, 1007 (1988).
P. M. Lukin, A. B. Zolotoi, S. V. Konovalikhin, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 1450 (1986).
Yu. V. Zefirov and P. M. Zorkii, Zh. Strukt. Khim.,15, 118 (1974).
H. A. Bent, Chem. Rev.,61, 275 (1961).
K. Leiserowitz, Acta Crystallogr.,B32, 775 (1976).
L. F. Fieser and M. Fieser, Organic Chemistry, 3rd ed., Reinhold, New York (1956).
V. I. Andrianov, Z. Sh. Safina, and B. L. Tarnopol'skii, Roentgen-75. An Automated Suite of Programs for Calculating Crystal Structure [in Russian], Chernogolovka (1975).
A. N. Chekhlov, Kristallografiya,26, 596 (1981).
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For previous communication, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2561—2566, November, 1988.
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Zolotoi, A.B., Zil'berg, S.P., Lukin, P.M. et al. Chemistry of 1,1,2,2-tetracyanoethane. 12. Condensation of 1,1,2,2-tetracyanoethane with crotonaldehyde in alcoholic solution. Russ Chem Bull 37, 2311–2314 (1988). https://doi.org/10.1007/BF00959885
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DOI: https://doi.org/10.1007/BF00959885