Russian Journal of Organic Chemistry

, Volume 40, Issue 1, pp 67–78 | Cite as

Regioselectivity in the Addition of 1,3-Dipolarophiles to 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes

  • A. P. Molchanov
  • D. I. Sipkin
  • Yu. B. Koptelov
  • J. Kopf
  • R. R. Kostikov
Article

Abstract

Thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of 1,3-dipolarophiles having an unsymmetrically substituted double C=C bond (such as N-arylimides derived from 2-aryl-substituted maleic, citraconic, and itaconic acids, ethyl propynoate, aryl isocyanates, and aryl isothiocyanates) leads to formation of the corresponding 1,3-dipolar cycloaddition products. The reaction is regioselective, and in most cases only one regioisomer is obtained. The addition direction depends on the 1,3-dipolarophile structure, i.e., electronic and steric factors determining the most effective orbital interaction upon approach of the reagent to substrate.

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Copyright information

© MAIK “Nauka/Interperiodica” 2004

Authors and Affiliations

  • A. P. Molchanov
    • 1
  • D. I. Sipkin
    • 1
  • Yu. B. Koptelov
    • 1
  • J. Kopf
    • 2
  • R. R. Kostikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institut fur anorganische ChemieHamburgGermany

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