Conclusions
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1.
Based on a study of the transformations of the addition products of amines to substituted 1-bromodiacetylenes a scheme was proposed for the mechanism of the nucleophilic reactions of the latter with primary and secondary amines.
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2.
Data were obtained to support the fact that the reactions with secondary amines, which lead to the formation of dialkylaminodiynes, proceed by the “addition-cleavage” mechanism.
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Literature cited
B. P. Gusev and V. F. Kucherov, USSR Patent 241, 451, March 11, 1968; Byull. Izobr., No. 14 (1969).
B. P. Gusev, L. A. Tsurgozen, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 1098 (1972).
H. G. Viehe, Chemistry of Acetylenes, New York (1969).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1076–1079, May, 1973.
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Gusev, B.P., Gorlova, E.K. & Kucherov, V.K. Reaction of substituted 1-bromodiacetylenes with primary and secondary amines. Russ Chem Bull 22, 1033–1036 (1973). https://doi.org/10.1007/BF00854244
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DOI: https://doi.org/10.1007/BF00854244