Conclusions
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1.
Conjugated monoene and diene aldehydes react with equimolar quantities of acetone cyanohydrin and diethylamine, giving β,γ-unsaturated cyanamines. With excess acetone cyanohydrin, these cyanamines are subsequently hydrogenated, forming 3,3-substituted 3-cyanoaminonitriles.
The analogous reaction of a triene aldehyde does not depend on the quantity of acetone cyanohydrin; the reaction leads to the cyanenamine.
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L. A. Yanovskaya, Kh. Shakhidayatov (Ch. Shahidayatov), E. P. Prokof'ev (Prokofiev), G. M. Andrianova, and V. F. Kucherov, Tetrahedron,24, 4677 (1968).
Kh. Shakhidayatov, L. A. Yanovskaya, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 953 (1969).
G. M. Zhdankina, G. V. Kryshtal', V. I. Andrusyak, V. S. Bogdanov, V. I. Kadentsev, O. S. Chizhov, and L. A. Yanovskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 615 (1980).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 346–350, February, 1982.
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Zhdankina, G.M., Kryshtal', G.V., Bogdanov, V.S. et al. Reaction of unsaturated aldehydes with acetone cyanohydrin in the presence of diethylamine. Russ Chem Bull 31, 313–316 (1982). https://doi.org/10.1007/BF00948247
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DOI: https://doi.org/10.1007/BF00948247