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Hypohalogenation of vinyl- and allylacetylenes and some chemical transformations of the products

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Abstract

Hypohalogenation of 2-methylhex-5-en-3-yn-2-ol, 2-methylhept-6-en-3-yn-2-ol, and their methyl ethers at 303–328 K with hydrochloric or hydrobromic acid in the presence of hydrogen peroxide involves only the double bond to produce the corresponding halohydrins in fairly high yields. Kinetic parameters of these reactions were determined, and the allylacetylenic alcohol and its methyl ether were found to be more reactive than their vinylacetylenic analogs. Acetylenic halohydrins and oxiranes derived therefrom were shown to be quite reactive compounds which may be used as building blocks in organic synthesis.

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Authors and Affiliations

  1. Institute of Polymeric Materials, National Academy of Sciences of Azerbaidjan, ul. S. Vurguna 124, Sumgait, 5004, Azerbaidjan

    M. G. Veliev & M. I. Shatirova

  2. Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaidjan, Baku, Azerbaidjan

    O. A. Sadygov & Kh. M. Alimardanov

Authors
  1. M. G. Veliev
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  2. O. A. Sadygov
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  3. Kh. M. Alimardanov
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  4. M. I. Shatirova
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Additional information

Original Russian Text © M.G. Veliev, O.A. Sadygov, Kh.M. Alimardanov, M.I. Shatirova, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 11, pp. 1609–1616.

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Veliev, M.G., Sadygov, O.A., Alimardanov, K.M. et al. Hypohalogenation of vinyl- and allylacetylenes and some chemical transformations of the products. Russ J Org Chem 43, 1604–1611 (2007). https://doi.org/10.1134/S1070428007110036

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  • DOI: https://doi.org/10.1134/S1070428007110036

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