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2-Carene in the Prins reaction

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Abstract

The Prins reaction of 2-carene with formaldehyde has been studied. The main reaction product is 2-hydroxymethyl-3-carene. The dehydration of 2-hydroxy-methyl-3-carene is accompanied by a skeletal rearrangement of the carane structure with the formation of products having a seven-membered ring.

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Literature cited

  1. S. Juonen and R. Hiltunen, Farm. Aikak.,83, 71 (1974).

    Google Scholar 

  2. French Patent No. 2,381,742.

  3. J. Chlebinski and B. Burczuk, Tetrahedron Lett., No. 19, 4775 (1970).

  4. N. G. Bhat, P. P. Pai, and C. H. Kulkarni, Indian J. Chem.,19, 316 (1980).

    Google Scholar 

  5. G. Ohloff, Ann. Chem., 79 (1959).

  6. É. N. Manukov, O. G. Vyglazov, and I. A. Shingel', Izv. Akad. Nauk BSSR, Ser. Khim. Nauk, 67 (1986).

  7. É. N. Manukov, O. G. Vyglazov, V. A. Chuiko, and I. A. Shingel', Zh. Org. Khim.,21, 2089 (1985).

    Google Scholar 

  8. R. Hoffmann, Tetrahedron Lett., 2907 (1970).

  9. G. Ohloff, Tetrahedron Lett., 3795 (1965).

  10. É. N. Manukov and T. R. Urbanovich, Iz. Akad. Nauk BSSR, Ser. Khim. Nauk, 70 (1985).

  11. B. G. Udarov, É. N. Manukov, O. G. Vyglazov, V. A. Chuiko, and L. V. Izotova, Khim. Prir. Soedin., 427 (1986).

  12. G. Ohloff, K. H. Schulte-Elte, and W. Giersch, Helv. Chim. Acta.,48, 1665 (1965).

    Google Scholar 

  13. G. Ohloff, H. Farnow, and W. Phillip, Ann. Chem., 43 (1958).

  14. C. J. Schmidle and R. C. Mansfeeld, J. Am. Chem. Soc.,78, 180 (1956).

    Google Scholar 

  15. Organic Reactions [Russian translation], Moscow, Vol. 11 (1963), p. 360.

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Authors
  1. É. N. Manukov
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  2. T. R. Urbanovich
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  3. O. G. Vyglazov
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  4. V. A. Chuiko
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  5. E. D. Skakovskii
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Additional information

Institute of Physical Organic Chemistry, Belorussian SSR Academy of Sciences, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 193–198, March–April, 1989.

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Manukov, É.N., Urbanovich, T.R., Vyglazov, O.G. et al. 2-Carene in the Prins reaction. Chem Nat Compd 25, 164–168 (1989). https://doi.org/10.1007/BF00598403

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  • DOI: https://doi.org/10.1007/BF00598403

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