Synthesis 2017; 49(05): 1103-1108
DOI: 10.1055/s-0036-1588616
paper
© Georg Thieme Verlag Stuttgart · New York

Safe and Convenient Synthesis of Primary N-Nitramines in the Freon Media

Autor*innen

  • Mikhail N. Zharkov

    a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp., 119991 Moscow, Russian Federation
  • Ilya V. Kuchurov

    a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp., 119991 Moscow, Russian Federation
  • Igor V. Fomenkov

    a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp., 119991 Moscow, Russian Federation
  • Vladimir A. Tartakovsky

    a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp., 119991 Moscow, Russian Federation
  • Ivan V. Fedyanin

    b   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., 119991 Moscow, Russian Federation   eMail: zlotin@ioc.ac.ru
  • Sergei G. Zlotin*

    a   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp., 119991 Moscow, Russian Federation
Weitere Informationen

Publikationsverlauf

Received: 27. Juli 2016

Accepted after revision: 10. September 2016

Publikationsdatum:
12. Oktober 2016 (online)


Graphical Abstract

Abstract

A convenient one-pot synthesis of primary aliphatic N-nitramines, which includes the nitration of available N,N′-dialkyloxalamides or N-alkylcarbamates with dinitrogen pentoxide in the 1,1,1,2-tetrafluoroethane media followed by ammonolysis of intermediate N-nitroamides in the same solvent has been developed. The method is environmentally safe, and affords target N-nitramines in up to 94% overall yield.

Supporting Information