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Sterically hindered inversion of nitrogen atoms in cyclic hydrazines:N,N′-dialkyl-1,3,4-oxadiazolidines; 1,3,4-thiadiazolidine; and 4,5-benzo-1,2,3,6-tetrahydropyridazine

  • Asymmetric Nitrogen
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Russian Chemical Bulletin Aims and scope

Abstract

N,N′-Diisopropyl-substituted 1,3,4-oxadiazolidine3c, 1,3,4-thiadiazolidine6, 4,5-benzo-1,2,3,6-tetrahydropyridazine8, and new 3,4-dialkyl-1,3,4-oxadiazolidines9–14 were synthesized and studied. The configurational stability of the N atoms does not change on going from compound3c to itsS-analog6 and decreases in the case of pyridazine8. 3,4-Di-tert-alkyl-1,3,4-oxadiazolidines3d and11–14 were found to be promising objectes for optical resolution.

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Authors and Affiliations

  1. N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 117977, Moscow, Russian Federation

    R. G. Kostyanovsky, Yu. I. El'natanov, G. K. Kadorkina, G. A. Nikiforov, I. I. Chervin, S. V. Usachev & V. R. Kostyanovsky

  2. Institute of Organic Chemistry, University of Essen, Germany

    P. Rademacher

Authors
  1. R. G. Kostyanovsky
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  2. P. Rademacher
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  3. Yu. I. El'natanov
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  4. G. K. Kadorkina
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  5. G. A. Nikiforov
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  6. I. I. Chervin
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  7. S. V. Usachev
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  8. V. R. Kostyanovsky
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Additional information

For Part 77, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1346–1354, July, 1997.

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Kostyanovsky, R.G., Rademacher, P., El'natanov, Y.I. et al. Sterically hindered inversion of nitrogen atoms in cyclic hydrazines:N,N′-dialkyl-1,3,4-oxadiazolidines; 1,3,4-thiadiazolidine; and 4,5-benzo-1,2,3,6-tetrahydropyridazine. Russ Chem Bull 46, 1291–1299 (1997). https://doi.org/10.1007/BF02495930

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  • DOI: https://doi.org/10.1007/BF02495930

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