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Reactions of alkyl hetaryl ketones with carbon tetrachloride under liquid/solid phase-transfer catalysis conditions

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Chemistry of Heterocyclic Compounds Aims and scope

Summary

Reactions of methyl and ethyl hetaryl ketones in the CCl4/solid KOH system in the presence of 18 crown-6 at room temperature yield the corresponding 2-hetaryl-2-trichloromethyloxiranes in 8–22% yields. Reactions of sterically hindered ketones of the type (hetaryl)COCHR2 (R = Me, Et) with CCl4/OH- form the corresponding a-hydroxy ketones of the type (hetaryl)COC(OH)R2 in 28–44% yields.

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References

  1. C. Y. Meyers, A. M. Malte, and W. S. Matthews, J. Am. Chem. Soc.,91, 7510 (1969).

    Google Scholar 

  2. R. T. Arnold and S. T. Kulenovic, J. Org. Chem.,43, 3687 (1978).

    Google Scholar 

  3. C. Y. Meyers and V. M. Kolb, J. Org. Chem.,43, 1985 (1978).

    Google Scholar 

  4. R. R. Regis and A. M. Doweyko, Tetrah. Lett.,23, 2539 (1982).

    Google Scholar 

  5. M. Makosza, B. Serafimova, and I. Gajos, Rocz. Chem.,43, 671 (1969).

    Google Scholar 

  6. M. Makosza and M. Fedorynski, Rocz. Chem.,49, 1779 (1975).

    Google Scholar 

  7. A. Jonczyk, A. Kwast, and M. Makosza, J. Org. Chem.,44, 1192 (1979).

    Google Scholar 

  8. S. E. Lauritzen, C. Romming, and L. Skattebol, Acta Chem. Scand. Ser. B,B35, 263 (1981).

    Google Scholar 

  9. W. P. Reeves and M. W. Creswell, Synth. Commun.,13, 945 (1983).

    Google Scholar 

  10. W. P. Reeves, M. W. Cresswell, D. S. Glass, and G. M. Sheide, Israel I. Chem.,26, 225 (1985).

    Google Scholar 

  11. M. Makosza, A. Kwast, E. Kwast, and A. Jonczyk, J. Org. Chem.,50, 3722 (1985).

    Google Scholar 

  12. I. E. Dolgii and E. B. Shvedova, Authors Certificate 1212007 USSR; Chem. Abstracts,109, 190226 (1988).

    Google Scholar 

  13. Eur. Pat. 197404; Chem. Abstracts, 106, 32575 (1987).

  14. Eur. Pat. 3002; Chem. Abstracts, 92, 94889 (1980).

  15. USA Pat. 4321118; Chem. Abstracts, 96, 218820 (1982).

    Google Scholar 

  16. Y. L. Pascal, Ann. Chim.,14, 245 (1968).

    Google Scholar 

  17. Organic Synthesis, Vol. 12, John Wiley and Sons, New York (1932), p. 62.

  18. E. M. Abele, Yu. Sh. Gol'dberg, Yu. Yu. Popelis, and M. V. Shimanskaya, Zh. Org. Khim.,26, 1784 (1990).

    Google Scholar 

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, LV-1006, Riga

    É. Abele, K. Rubina, Yu. Popelis, Yu. Gol'dberg & M. Szymanska

Authors
  1. É. Abele
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  2. K. Rubina
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  3. Yu. Popelis
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  4. Yu. Gol'dberg
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  5. M. Szymanska
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 312–315, March, 1994.

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Abele, É., Rubina, K., Popelis, Y. et al. Reactions of alkyl hetaryl ketones with carbon tetrachloride under liquid/solid phase-transfer catalysis conditions. Chem Heterocycl Compd 30, 275–278 (1994). https://doi.org/10.1007/BF01165690

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  • DOI: https://doi.org/10.1007/BF01165690

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