Download PDF
Synthesis 2004(16): 2609-2610  
DOI: 10.1055/s-2004-831221
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

The First Synthesis of 1,1-Dinitrocyclopropane

Ekaterina M. Budynina, Elena B. Averina, Olga A. Ivanova, Nikolai V. Yashin, Tamara S. Kuznetsova*, Nikolai S. Zefirov
Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russia
Fax: +7(095)9390290; e-Mail: kuzn@org.chem.msu.ru;
Further Information

Publication History

Received 25 May 2004
Publication Date:
16 September 2004 (online)

    Permissions and Reprints All articles of this category

Corrected by:

The First Synthesis of 1,1-DinitrocyclopropaneSynthesis 2004; 2004(17): 2942-2942
DOI: 10.1055/s-2004-834886

Abstract

1,1-Dinitrocyclopropane was prepared in 62% yield. This high energetic compound was previously unknown. Herein its preparation via tandem reaction between nitroform and diazo­methane in benzene is described.

Key words

1,1-dinitrocyclopropane - trinitromethane - diazo­methane - tandem reactions - alicyclic nitro compounds

    References

  • 1 Chemistry of energetic materials   Olah GA. Squire DR. Academic Press, Inc.; New York: 1991. 
    Google Scholar
  • 2 Carbocyclic Three- and Four-Membered Ring Compounds: In Houben-Weyl Methods of Organic Chemistry   Vol. E 17c:  de Meijere A. Thieme; Stuttgart: 1997. 
    Google Scholar
  • 3 Wade PA. Daily WP. Carroll PJ. J. Am. Chem. Soc.  1987,  109:  5452 
    CrossrefGoogle Scholar
  • 4 Tartakovski VA. Gribov BG. Savost’yanova IA. Novikov SS. Izv. Akad. Nauk, Ser. Khim.  1965,  9:  1644 ; Chem. Abstr. 1966, 64, 2080c
    Google Scholar
  • 5 Kai Y. Knochel P. Kwiatkowski S. Dunitz JD. Oth JFM. Seebach D. Kalinowski HO. Helv. Chim. Acta  1982,  65:  137 
    CrossrefGoogle Scholar
  • 6 O’Bannon PE. Dailey WP. Tetrahedron  1990,  46:  7341 
    CrossrefGoogle Scholar
  • 7 Chlenov IE. Kashutina MV. Ioffe SL. Novikov SS. Tartakovski VA. Izv. Akad. Nauk, Ser. Khim.  1969,  9:  2085 ; Chem. Abstr. 1970, 72, 12627j
    Google Scholar
  • 9a Onischenko AA. Chlenov IE. Makarenkova LM. Tartakovski VA. Izv. Akad. Nauk, Ser. Khim.  1971,  7:  1560 ; Chem. Abstr. 1971, 75, 98480c
    Google Scholar
  • 9b Tartakovski VA. Chlenov IE. Lagodzinskaya GV. Novikov SS. Dokl. Akad. Nauk.  1965,  161:  136 ; Chem. Abstr. 1967, 67, 53206m
    Google Scholar
  • 9c Onischenko AA. Tartakovski VA. Izv. Akad. Nauk, Ser. Khim.  1970,  4:  948 ; Chem. Abstr. 1970, 73, 34718n
    Google Scholar
  • 10a Zeldin L. Shechter H. J. Am. Chem. Soc.  1957,  79:  4708 
    Google Scholar
  • 10b Fridman AL. Gabitov FA. Surkov VD. Zh. Org. Khim.  1972,  8:  2457 ; Chem. Abstr. 1973, 78, 83543p
    Google Scholar
8

To be reported separately.

11

Separation of the reaction mixture by column chromatography (silica gel, n-hexane-CHCl3, 3:1) led to partial decomposition of 1.