Abstract
The corresponding acetylenic aziridino hydroxy carbinols were obtained by the reaction of aziridine, 2,2-dimethylaziridine, and methyl aziridine-2-carboxylate with 4-hydroxy-4-methylpent-2-yn-1-al and 3-(1-hydroxycyclohexyl)prop-2-yn-1-al. It is shown that the latter at room temperature undergo isomerization with time to 2-hydroxy-4-aziridino-5,5-dialkylduiydrofurans. The isomerization of acetylenic aziridinocarbinols, which includes an intermediate step involving retrodecomposition of the aziridino (hydroxy) carbinols to the starting aldehydes and aziridines, was investigated by dynamic NMR spectroscopy.
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A. V. Eremeev, D. A. Tikhomirov, and é. é. Liepin'sh, Khim. Geterotsikl. Soedin., No. 2, 207 (1977).
A. S. Medvedeva, L. P. Safronova, I. D. Kalikhman, and M. G. Voronkov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1799 (1976).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 334–337, March, 1979.
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Eremeev, A.V., Tikhomirov, D.A. & Shubina, Y.V. Reaction of aziridines with acetylenic γ-hydroxy aldehydes. Chem Heterocycl Compd 15, 273–276 (1979). https://doi.org/10.1007/BF00474090
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DOI: https://doi.org/10.1007/BF00474090