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Cyanoacetylene and Its Derivatives: XXVI. Hydrohalogenation of 4-Alkyl-4-hydroxy-2-alkynenitriles

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Abstract

The reaction of 4-alkyl-4-hydroxy-2-alkynenitriles with hydrogen halides (HCl and HI) in dioxane is accompanied by intramolecular cyclization with formation of 5,5-dialkyl-4-halo-2-imino-2,5-dihydrofuran hydrohalides. Treatment of the latter with K2CO3 in ethanol yields 5,5-dialkyl-4-halo-2-imino-2,5-dihydrofurans.

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Authors and Affiliations

  1. Siberian Division, Russian Academy of Sciences, Favorskii Irkutsk Institute of Chemistry, ul. Favorskogo 1, Irkutsk, 664033, Russia

    A. G. Mal'kina, V. V. Nosyreva, R. N. Kudyakova, L. V. Sokolyanskaya & B. A. Trofimov

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  1. A. G. Mal'kina
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  2. V. V. Nosyreva
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  3. R. N. Kudyakova
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  4. L. V. Sokolyanskaya
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  5. B. A. Trofimov
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Mal'kina, A.G., Nosyreva, V.V., Kudyakova, R.N. et al. Cyanoacetylene and Its Derivatives: XXVI. Hydrohalogenation of 4-Alkyl-4-hydroxy-2-alkynenitriles. Russian Journal of Organic Chemistry 37, 649–654 (2001). https://doi.org/10.1023/A:1012435430971

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  • DOI: https://doi.org/10.1023/A:1012435430971

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