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Conjugated oxidation of the vinylacetylene system during intramolecular cyclization of 4-carbethoxy-5-ketohexeh-3-yne

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A furancarboxaldehyde, 5-methyl-4-carbethoxyfurfural (III), is formed from 4-carbethoxy-5-keto-hexen-3-yne (I) by the action of different oxidizing agents: HClO4 and its salts, H2O2 and hydroperoxides. Molecular oxygen, AcOOH, and stable hydroperoxides do not oxidize (I).

  2. 2.

    Furancarboxaldehyde is formed only in systems able to protonate the acetylenic bond in (I). Furfuryl alcohol (IIc) thus formed is not an intermediate product during the formation of furancarboxaldehyde (III).

  3. 3.

    A possible mechanism of oxidation is suggested, which includes successive stages of protonation of (I), cyclization of the vinyl acetylene system, and disproportionation of the labile intermediate product, leading to furancarboxaldehyde.

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Literature cited

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Authors and Affiliations

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

    I. A. Esikova, S. S. Yufit & V. F. Kucherov

Authors
  1. I. A. Esikova
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  2. S. S. Yufit
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  3. V. F. Kucherov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2750–2754, December, 1977.

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Esikova, I.A., Yufit, S.S. & Kucherov, V.F. Conjugated oxidation of the vinylacetylene system during intramolecular cyclization of 4-carbethoxy-5-ketohexeh-3-yne. Russ Chem Bull 26, 2543–2546 (1977). https://doi.org/10.1007/BF00924561

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  • DOI: https://doi.org/10.1007/BF00924561

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