Asymmetric nitrogen

Communication 50. Nature of the effect of substituents attached to the C atom on the reactivities of diaziridines; synthesis and photoelectronic spectra of functionally substituted 1,N-diazabicyclo[M.1.0]alkanes
  • G. V. Shustov
  • S. N. Benisenko
  • R. G. Kostyanovskii
Organic Chemistry


  1. 1.

    The energy of the highest occupied MO and, consequently, the nucleophilic reactivities of diaziridines are determined primarily by the inductive effect of the substituent attached to the C atom.

  2. 2.

    The possibility of the synthesis of 5-substituted 1,6-diazabicyclo[3.1.0]hexanes by epimination of the corresponding Δ1-pyrrolines is limited by the type of substituent in the 2 position in the latter: bulky and π-donor substituents hinder the formation of a diaziridine ring, whereas the strongly electronegative CN group promotes facile rearrangement of the intermediately formed diaziridine to the corresponding hydrazone.



Nitrogen Hexane Hydrazone Inductive Effect Nucleophilic Reactivity 
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Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • G. V. Shustov
    • 1
  • S. N. Benisenko
    • 1
  • R. G. Kostyanovskii
    • 1
  1. 1.Institute of Chemical PhysicsAcademy of Sciences of the USSRMoscow

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