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Some transformations of acetylenic alcohol epoxides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown that the hydration of acetylenic alcohol epoxides containing an epoxide ring in the β position relative to the triple bond in the presence of sulfuric acid leads to the formation of acetylenic triols: 6-methyl-4-heptyne-1,2,6-, 7-methyl-5-octyne-2,3,7-, 2,7-dimethyl-5-octyne-2,3,7-, and 2,3,7-trimethyl-5-octyne-2,3,7-triols. It was established that the hydration process is hampered as the number of alkyl substituents attached to the epoxide ring increases. The triols were subjected to intramolecular cyclization under the influence of mercuric chloride to the corresponding chloromercurated derivatives of furan: 2-(1-chloromercuri-2-methyl-1-propenyl) and 5-methyi-2-(1-chloromercuri-2-methyl-1-propenyl)furans. The IR and PMR spectral data are presented.

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Authors and Affiliations

  1. Dnepropetrovsk State University, 320625, Dnepropetrovsk

    N. N. Baranov, M. S. Malinovskii & M. P. Khmel

Authors
  1. N. N. Baranov
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  2. M. S. Malinovskii
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  3. M. P. Khmel
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1164–1167, September, 1977.

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Baranov, N.N., Malinovskii, M.S. & Khmel, M.P. Some transformations of acetylenic alcohol epoxides. Chem Heterocycl Compd 13, 934–937 (1977). https://doi.org/10.1007/BF00472440

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  • DOI: https://doi.org/10.1007/BF00472440

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