Chemistry of Heterocyclic Compounds

, Volume 7, Issue 3, pp 349–354 | Cite as

Synthesis and transformations of 6,6,7,7-tetramethyl-2-quinuclidone

  • E. I. Levkoeva
  • E. S. Nikitskaya
  • L. N. Yakhontov
Article
  • 38 Downloads

Abstract

6,6,7,7-Tetramethyl-2-quinuclidone was synthesized, and its differences from the usual amides were shown. It enters into three types of chemical reactions: 1) the N-CO bond is broken under the influence of protic nucleophilic agents (water, alcohols, amines, hydroxylamine, and hydrazines), and nucleophilic agents are acylated by the (2,2,6,6-tetramethyl-4-piperidyl)-acetic acid residue; 2) the N-C(CH3)2 bond is broken by reaction with nucleophilic agents in aprotic media (phenyllithium in ether, PCl5 in benzene, acetone cyanohydrin, and LiAlH4 in ether) to form 4-substituted 6,6-dimethyl-2-piperidones; 3) reactions with the preservation of the quinuclidine ring occur on treatment with electrophilic reagents (hydrogen chloride and methyl iodide) in aprotic solvents and during reduction.

Keywords

Ether Acetone Benzene Acetic Acid Amide 

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Literature cited

  1. 1.
    R. Lukes, Coll. Czech. Chem. Comm.,10, 148 (1938).Google Scholar
  2. 2.
    F. S. Fawcett, Chem. Rev.,47, 220 (1950).Google Scholar
  3. 3.
    L. N. Yakhontov and M. V. Rubtsov, Zh. Obshch. Khim.,27, 72 (1957).Google Scholar
  4. 4.
    H. Pracejus, Chem. Ber.,92, 988 (1959);98, 2898 (1965).Google Scholar
  5. 5.
    H. Pracejus, M. Kehlen, H. Kehlen, and H. Matschiner, Tetrahedron,21, 2257 (1965).Google Scholar
  6. 6.
    R. G. Kostyanovskii, E. E, Mikhlina, E. I. Levkoeva, and L. N. Yakhontov, Org. Mass Spectrometry,3, 1023 (1970).Google Scholar
  7. 7.
    L. N. Yakhontov, L. I. Mastafanova, K. F. Turchin, Yu. N. Sheinker, and M. V. Rubtsov, Dokl. Akad. Nauk SSSR,168, 1085 (1966).Google Scholar
  8. 8.
    L. Bellamy, Infrared Spectra of Complex Molecules, Methuen (1958).Google Scholar
  9. 9.
    I. Ritter and P. Minieri, J. Am. Chem. Soc.,70, 4045 (1948).Google Scholar
  10. 10.
    R. G. Kostyanovskii, I. I. Chervin, and T. Z. Papoyan, Izv. Akad. Nauk SSSR, 2399 (1968).Google Scholar
  11. 11.
    G. P. Chernysh, Master's Dissertation [in Russian], M. V. Lomonosov Moscow Institute of Fine Chemical Technology (1968).Google Scholar
  12. 12.
    F. S. Kipping and T. Greasley, J. Chem. Soc.,124, 2611 (1924).Google Scholar

Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1973

Authors and Affiliations

  • E. I. Levkoeva
    • 1
  • E. S. Nikitskaya
    • 1
  • L. N. Yakhontov
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical ChemistryMoscow

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