Reactions of some halocetylenes with sodium amide

M. S. Shavartsberg, S. F. Vasilevskii, A. N. Sinyakov

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Abstract

1. The action of sodium amide in ammonia on 4-chloroethynyl-N-alkylpyrazoles having a methyl group at position 5 leads to the formation of rearranged substitution products, i.e., the respective 5-(aminomethyl)-pyrazolylacetylenes. A suggestion is made about the mechanism of the reaction. 2. Under the same conditions 4-bromo- or 4-iodoethynyl-5-methylpyrazoles, like phenylchloroacetylene, exchange the halogen atom for sodium. At the same time a small amount of the aryl- or heteroarylacetonitrile is formed.

Original language	English
Pages (from-to)	2138-2141
Number of pages	4
Journal	Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume	25
Issue number	10
DOIs	https://doi.org/10.1007/BF02659534
Publication status	Published - 1 Oct 1976
Externally published	Yes

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ASJC Scopus subject areas

Chemistry(all)

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Shavartsberg, M. S., Vasilevskii, S. F., & Sinyakov, A. N. (1976). Reactions of some halocetylenes with sodium amide. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 25(10), 2138-2141. https://doi.org/10.1007/BF02659534

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N2 - 1. The action of sodium amide in ammonia on 4-chloroethynyl-N-alkylpyrazoles having a methyl group at position 5 leads to the formation of rearranged substitution products, i.e., the respective 5-(aminomethyl)-pyrazolylacetylenes. A suggestion is made about the mechanism of the reaction. 2. Under the same conditions 4-bromo- or 4-iodoethynyl-5-methylpyrazoles, like phenylchloroacetylene, exchange the halogen atom for sodium. At the same time a small amount of the aryl- or heteroarylacetonitrile is formed.

AB - 1. The action of sodium amide in ammonia on 4-chloroethynyl-N-alkylpyrazoles having a methyl group at position 5 leads to the formation of rearranged substitution products, i.e., the respective 5-(aminomethyl)-pyrazolylacetylenes. A suggestion is made about the mechanism of the reaction. 2. Under the same conditions 4-bromo- or 4-iodoethynyl-5-methylpyrazoles, like phenylchloroacetylene, exchange the halogen atom for sodium. At the same time a small amount of the aryl- or heteroarylacetonitrile is formed.

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10.1007/BF02659534