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Preparation of 1,2=dialkylcycloalkanes synthesisis of the stereoisomeric 1-butyl-2-methylcyclopentanes

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    A suitable p~reparative method has been proposed for obtaining 2-methylcyclopentanone: it consists in the dehydration of the diol obtained b y oxidizing 1-methylcyclopentene with a mixture of hydrogen peroxide and formic acid.

  2. 2.

    It has been shown that this method is of no value for the preparation of 2-methylcyclohexanone: in the case of the six-membered cycle, dehydration of the diol is accompanied by isomerization side reaction.

  3. 3.

    1-Butyl-2-methyleyclopentane has been synthesized from 2-methylcyclopentanone prepared by the above method, and it has been separated into its cis and trans isomers.

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Literature cited

  1. G. S. Landsberg and B. A. Kazansky, Bull. Acad. Sci. U.S.S.R., Div. Chem. Sci., No. 2, 100 (1951).

  2. B. A. Kazansky, A. V. Koperina, and O. A. Zemskaya, J. Gen Chem., 20, 1212 (1950).

    Google Scholar 

  3. N. D. Zelinsky and E. S. Przhevalsky, J. Russ. Chem. Soc., 37, 628 (1905).

    Google Scholar 

  4. M. Rysselberge, Bull. Soc. chim. Belg. 35, 311 (1926).

    Google Scholar 

  5. R. Cornubert, Ch. Borrel, Bull. Soc. chim. (4), 47, 301 (1930).

    Google Scholar 

  6. G. A. Lutz A. E. Bearse, J. E. Leonard, F. C. Croxton, J. Am. Chem. Soc. 70, 4139 (1948).

    Google Scholar 

  7. M. Tiffeneau, B. Tchoubar, Compt. rend. 199, 1624 (1934).

    Google Scholar 

  8. N. D. Zelinsky and Yu. A. Arbuzov, Proc. Acad. Sci. U.S.S.R., 23, 793 (1939).

    Google Scholar 

  9. Ya. I. Denisenko and A. D. Frolova, Bull. Acad. Sci. U.S.S.R. Div. Chem. Sci. 5, 361 (1944).

    Google Scholar 

  10. G. Chiurdoglu, Bull. Soc. chim. Belg., 43, 35 (1934); 44, 527 (1935); Bull. Acad. Roy. Belg. Classe Sciences (5) 17, 1404 (1932).

    Google Scholar 

  11. Org. Syntheses, 28, 35 (1948).

  12. H. Adkins, A. K. Roebuck, J. Am. Chem. Soc., 70, 4041 (1948).

    Google Scholar 

  13. Ya. I. Denisenko and A. D. Haber, Bull. Acad. Sci. U.S.S.R., Div. Chem. Sci. No. 1, 35 (1945).

  14. K. C. Edson, J. S. Powell, E. L. Fisher, Ind. Eng. Chem. 40, 1526 (1948).

    Google Scholar 

  15. N. D. Zelinsky and P. Ya. Levina, Ber. 66, 477 (1933).

    Google Scholar 

  16. L. F. Gutt, Ber. 40, 2062 (1907); N. A. Menshutkin, J. Chem. Soc., 89, 534 (1906); K. AuWers, R. Hinterseber, W. Trappmann, Ann. 410, 274 (1915).

    Google Scholar 

  17. G. Egloff, Physical Constants of Hydrocarbons, v. II, 326.

  18. N. D. Zelinsky and A. Gorsky, J. Russ. Phys. Chem. Soc., 40, 1397 (1908); Ber. 41, 2630 (1908).

    Google Scholar 

  19. R. Horinti, H. Otuki, O. Okuda, Chem. Abstr., 34, 1983 (1940).

    Google Scholar 

  20. G. Chiurdoglu, Bull. Soc. chim. Belg. 47, 244 (1938).

    Google Scholar 

  21. A. Skita, Ber. 56, 1016 (1923).

    Google Scholar 

  22. B. A. Kazansky, A. L. Liberman, A. F. Plate, M. I. Rozengart, and O. D. Sterligov, Proc. Acad. Sci. U.S.S.R., 71, 477 (1950).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemistry of the USSR, Academy of Sciences, M. V. Lomonosov Moscow State University, USSR

    A. F. Plate, A. L. Liberman & N. A. Momma

Authors
  1. A. F. Plate
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  2. A. L. Liberman
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  3. N. A. Momma
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Plate, A.F., Liberman, A.L. & Momma, N.A. Preparation of 1,2=dialkylcycloalkanes synthesisis of the stereoisomeric 1-butyl-2-methylcyclopentanes. Russ Chem Bull 2, 617–623 (1953). https://doi.org/10.1007/BF01171783

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  • DOI: https://doi.org/10.1007/BF01171783

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