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Hydration of allenylacetylenic alcohols — New route to 6-methyl-2,3-dihydro-4-pyranones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The mercuric sulfate-catalyzed acidic hydration of allenylacetylenic alcohols leads to 6-methyl-2,3-dihydro-4-pyranones — products of cyclization of unsaturated β-diketones. In the case of 1-(3,4-pentadien-1-ynyl)cyclohexanol 2-(1-cyclohexenyl)-5-methylfuran is formed in addition to the corresponding dihydropyranone.

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Literature cited

  1. M. G. Voskanyan, Yu. M. Dangyan, G. A. Panosyan, and Sh. O. Badanyan, Arm. Khim. Zh., 36, 40 (1983).

    Google Scholar 

  2. A. P. Khrimyan, A. V. Karapetyan, and Sh. O. Badanyan, USSR Inventor's Certificate No. 706.413; Byull. Izobret., No. 48, 88 (1979).

  3. S. Gelin and R. Gelin, Bull. Soc. Chim. Fr., No. 1, 288 (1968).

    Google Scholar 

  4. I. I. Nazarova, B. P. Gusev, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1580 (1967).

    Google Scholar 

  5. J. W. Emsley, J. Feeney, and L. H. Sutcliffe, High-Resolution NMR Spectroscopy, Pergamon, Oxford (1965).

    Google Scholar 

  6. I. N. Nazarov and V. M. Romanov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 4, 559 (1940).

    Google Scholar 

  7. I. N. Nazarov, I. V. Torgov, and D. N. Terekhova, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 2, 205 (1947).

    Google Scholar 

  8. R. Morrison and R. Boyd, Organic Chemistry, Allyn and Bacon (1973).

  9. A. Sevin, W. Chodkiewicz, and P. Cadiot, Bull. Soc. Chim. Fr., Nos. 5–6, 913 (1974).

    Google Scholar 

  10. A. P. Khrimyan, A. V. Karapetyan, and Sh. O. Badanyan, Arm. Khim. Zh., 34, 40 (1981).

    Google Scholar 

  11. L. N. Vereshchagin, L. D. Gavrilov, E. I. Titova, and L. P. Vologdina, Zh. Org. Khim., 9, 276 (1974).

    Google Scholar 

  12. I. Ponticello and K. L. Furman, J. Polym. Sci., Polym. Chem. Ed., 12, 985 (1974).

    Google Scholar 

  13. Sh. O. Badanyan and K. L. Sarkisyan, Arm. Khim. Zh., 26, 817 (1973).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemistry, Academy of Sciences of the Armenian SSR, 375094, Yerevan

    A. P. Khrimyan, A. V. Karapetyan & Sh. O. Badanyan

Authors
  1. A. P. Khrimyan
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  2. A. V. Karapetyan
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  3. Sh. O. Badanyan
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Additional information

Communication 113 from the series “Reactions of unsaturated compounds.” See [1] for communication 112.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 619–622, May, 1984.

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Khrimyan, A.P., Karapetyan, A.V. & Badanyan, S.O. Hydration of allenylacetylenic alcohols — New route to 6-methyl-2,3-dihydro-4-pyranones. Chem Heterocycl Compd 20, 495–498 (1984). https://doi.org/10.1007/BF00514299

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  • DOI: https://doi.org/10.1007/BF00514299

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