Russian Chemical Bulletin

, Volume 42, Issue 2, pp 328–333 | Cite as

Synthesis and structure of diastereomeric trans-3,4-diamino-2,2,6,6-tetramethylpiperidine1-oxyl derivatives

  • V. D. Sen'
  • V. V. Tkachev
  • L. O. Atovmyan
Organic Chemistry


The reaction of 3,4-diamino-2,2,6,6-tetramethylpiperidine-1-oxyl with (1S)-(+)-camphor-10-sulfonyl chloride gives a mixture of diastereomeric 4-monosulfonylamino derivatives. The products of their acylation have been obtained. The 3,4-bis-[(1S)-camphor-10-sulfonylamino] derivative was synthesized and resolved to individual diastereomers. For one of them thetrans relationship of the 3- and 4-substituents and the absolute (3S,4R)-configuration were established by X-ray structural analysis.

Key words

trans-3.4-diamino-2,2,6,6-tetramethylpiperidine-1-oxyl diastereomeric derivatives, resolution structure absolute configuration 


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  1. 1.
    V. D. Sen',Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2094 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 1928].Google Scholar
  2. 2.
    A. T. Quintanilha and R. J. Mehlhorn,FEBS Lett, 1978,91, 104.Google Scholar
  3. 3.
    D. D. Perrin, B. Dempsey and E. P. Serjeant,pK a Prediction for Organic Acids and Bases, Champan and Hall, London, 1981, 30.Google Scholar
  4. 4.
    B. V. Rozynov, R. I. Zhdanov, O. S. Reshetova, N. G. Kapitanova, Z. L. Gordon, and E. G. Rozantsev,Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 1838 [Bull. Acad. Sci. USSR, Div.Chem.Sci.,1978,27, No. 8].Google Scholar
  5. 5.
    R. A. Alden, J. Krant, and T. G. Taylor,J. Am. Chem. Soc., 1968,90, 74.Google Scholar
  6. 6.
    A. B. Zolotoi, P. M. Lukin, S. V. Konovalikhin, M. Yu. Skvortsova, O. E. Nasakin, and L. O. Atovmyan,Khim. Geterotsykl. Soedin., 1991, 519 [Chem. Heterocycl. Comp., 1991 (Engl. Transl.)].Google Scholar
  7. 7.
    A. Albert and E. Serjeant,Ionization Constants of Acids and Bases, J. Wiley and Sons, New York, 1962, 179 p.Google Scholar

Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • V. D. Sen'
    • 1
  • V. V. Tkachev
    • 1
  • L. O. Atovmyan
    • 1
  1. 1.Institute of Chemical Physics in ChernogolovkaRussian Academy of SciencesChernogolovkaRussian Federation

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