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Stereochemistry of nucleophilic-addition reactions at the carbonyl group in cyclic ketones

Communication 5. Stereochemistry of cyanohydrin synthesis with 2-chlorocyclohexanone

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

Summary

  1. 1.

    The stereochemistry of the cyanohydrin synthesis was studied for the case of 2-chlorocyclohexanone.

  2. 2.

    The steric orientation of the entering cyanide ion depends on the reaction conformation of the original 2-chlorocyclohexanone.

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Literature cited

  1. I. N. Nazarov, A. A. Akhrem and A. V. Kamernitskii, Izv. AN SSSR, Otd. khim. n. 1958, 631.

  2. I. N. Nazarov, A. V. Kamernitskii and A. A. Akhrem, Zh. obsch. khimii28, 1458 (1958).

    Google Scholar 

  3. A. V. Kamernitskii and A. A. Akhrem, Izv. AN SSSR, Otd. khim. n. 1959, 740.

  4. A. V. Kamernitskii and A. A. Akhrem, Zh. obshch. khimii30, 754 (1960).

    Google Scholar 

  5. A. V. Kamernitskii and A. A. Akhrem, Uspekhi khimii30, 145 (1961).

    Google Scholar 

  6. J. P. Fourneau, R. Marechal, Bull. Soc. chim. France12, 990 (1945).

    Google Scholar 

  7. M. Mousseron, J. Jullien, Y. Jolchine, Bull. Soc. chim. France 1950, 1209.

  8. I. N. Nazarov, A. A. Akhrem and A. V. Kamernitskii, Zh. obshch. khimii25, 1345 (1955).

    Google Scholar 

  9. W. D. Emmons, A. S. Pagano, J. Amer. Chem. Soc.77, 89 (1955).

    Google Scholar 

  10. Stereochemistry of Cyclohexane Derivatives [Russian translation], IL, M., (1958).

  11. M. I. Batuev, A. A. Akhrem, A. V. Kamernitskii and A. D. Matveeva, Izv. AN SSSR, Otd. khim. n. 1961, 1813.

  12. E. Corey, J. Amer. Chem. Soc.75, 2301 (1953).

    Google Scholar 

  13. C. Djerassi, L. E. Geller, E. J. Eisenbraun, J. Organ. Chem.25, I (1960).

    Google Scholar 

  14. C. Castinel, G. Chiurdoglu, M. L. Josien, J. Lascomle, E. Vanlanduyt, Bull. Soc. chim. France 1958, 807.

  15. A. Cross, Introduction to Practical Infrared Spectroscopy [Russian translation], IL, M., 1961, p. 92.

    Google Scholar 

  16. L. F. Fieser, M. Fieser, Steroids, (N. Y., 1959), p. 269.

  17. R. Van Coillie, Bull. Soc. chim. France42, 419 (1933).

    Google Scholar 

  18. E. J. Boorman, R. P. Linstead, J. Chem. Soc. 1935, 261.

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Author information

Authors and Affiliations

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

    A. A. Akhrem, A. V. Kamernitskii & N. S. Pavlova-Grishina

Authors
  1. A. A. Akhrem
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  2. A. V. Kamernitskii
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  3. N. S. Pavlova-Grishina
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Additional information

For Communication 4 of this series, which was incorrectly numbered 6, see [4].

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Akhrem, A.A., Kamernitskii, A.V. & Pavlova-Grishina, N.S. Stereochemistry of nucleophilic-addition reactions at the carbonyl group in cyclic ketones. Russ Chem Bull 11, 984–989 (1962). https://doi.org/10.1007/BF00905218

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  • DOI: https://doi.org/10.1007/BF00905218

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