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

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
› Author Affiliations
Further Information

Publication History

Received: 27 July 2016

Accepted after revision: 10 September 2016

Publication Date:
12 October 2016 (online)


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

 
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