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Stereochemistry of additions to a triple bond

Communication 3. Stereochemistry of the addition of bromine to propargyl alcohols

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    The photochemical bromination of 2-propyn-1-ol gives mainly the trans-dibromide, whereas tertiary acetylenic alcohols and their acetic esters give mainly cis-dibromo compounds.

  2. 2.

    The trans -dibromides of tertiary acetylenic alcohols and their acetic esters are less stable than their cis-isomers and pass into these when irradiated or allowed to stand in the dark.

  3. 3.

    In the bromination of tertiary acetylenic alcohols in acetic acid, mixtures of dibromides are formed in which trans-isomers predominate. In presence of small amounts of lithium bromide in the dark, selective transbromination can be effected.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    I. N. Nazarov & L. D. Bergel'son

Authors
  1. I. N. Nazarov
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  2. L. D. Bergel'son
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Additional information

For Communications 1 and 2 see Zhur. Obshchei Khim.27, 1540 (1957);28, 1132 (1958). [See English translations].

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Nazarov, I.N., Bergel'son, L.D. Stereochemistry of additions to a triple bond. Russ Chem Bull 9, 826–833 (1960). https://doi.org/10.1007/BF01179182

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  • DOI: https://doi.org/10.1007/BF01179182

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