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Special features of 1,3-dipolar cycloaddition of n-methylazomethinylid to nitrobenzazoles

  • A. M. Starosotnikov
  • D. V. Khakimo
  • M. A. Bastrakov
  • S. Yu. Pechenkin
  • S. A. Shevelev
  • T. S. PivinaEmail author
Article

Synthetic approaches to 1,3-dipolar cycloaddition of N-methylazomethinylid to mononitrobenzazole are described. The geometric and electronic structures have been studied by quantum chemical methods (HF/STO-3 G and B3LYP/6-31 G*) and the reactivity indexes of compounds have been estimated. It was shown that 1,3-dipolar cycloaddition of N-methylazomethinylid to the dipolarophile has a polar character and proceeds in accordance with the normal (noninversion) electronic distribution.

Keywords

aromatic nitro compounds reactivity indexes quantum chemical calculations methods HF/STO-3 G and B3LYP/631 G* [3 + 2] cycloaddition mechanism of 1,3-dipolar cycloaddition 

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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • A. M. Starosotnikov
    • 1
  • D. V. Khakimo
    • 1
  • M. A. Bastrakov
    • 1
  • S. Yu. Pechenkin
    • 1
  • S. A. Shevelev
    • 1
  • T. S. Pivina
    • 1
    Email author
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of Sciences (RAN)MoscowRussia

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