Download PDF
Synthesis 2010(2): 259-266  
DOI: 10.1055/s-0029-1217103
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Diethyl [Nitro(diazo)methyl]phosphonate: Synthesis and Reactivity towards Alkenes

Andrey V. Chemagina, Nikolai V. Yashin*a,b, Yuri K. Grishina, Tamara S. Kuznetsovaa,b, Nikolai S. Zefirova,b
a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation
Fax: +7(495)9393969; e-Mail: yashin-n@org.chem.msu.ru;
b IPhAC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region, 142432, Russian Federation
Further Information

Publication History

Received 4 September 2009
Publication Date:
06 November 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

A novel and convenient synthesis of diethyl [nitro(di­azo)methyl]phosphonate and its reactions with various alkenes are described. The reactivity of diethyl [nitro(diazo)methyl]phosphonate is shown to be dependent on the structure of the alkene. A number of cyclopropyl α-nitrophosphonates were obtained.

Key words

diazo compounds - phosphonates - alkenes - cyclopropanation - carbenes

    References

  • 1 Sheridan RP. J. Chem. Inf. Comput. Sci.  2002,  42:  103 
    CrossrefGoogle Scholar
  • For comprehensive reviews, see:
  • 2a Ordóñez M. Rojas-Cabrera H. Cativiela C. Tetrahedron  2009,  65:  17 
    Google Scholar
  • 2b Kafarski B. Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem.  1991,  63:  193 
    Google Scholar
  • 2c Wolfenden R. Annu. Rev. Biophys. Bioeng.  1976,  5:  271 
    Google Scholar
  • 3 For a recent review, see: Brackmann F. de Meijere A. Chem. Rev.  2007,  107:  4493 
    CrossrefPubMedGoogle Scholar
  • 4a Erion MD. Walsh CT. Biochemistry  1987,  26:  3417 
    Google Scholar
  • 4b Groth U. Lehmann L. Richter L. Schöllkopf U. Liebigs Ann. Chem.  1993,  427 
    Google Scholar
  • 4c Yamazaki S. Takada T. Moriguchi Y. Yamabe S. J. Org. Chem.  1998,  63:  5919 
    Google Scholar
  • 4d Fadel A. J. Org. Chem.  1999,  64:  4953 
    Google Scholar
  • 4e Tesson N. Dorigneux B. Fadel A. Tetrahedron: Asymmetry  2002,  13:  2267 
    Google Scholar
  • 5a Yashin NV. Averina EB. Gerdov SM. Kuznetsova TS. Zefirov NS. Tetrahedron Lett.  2003,  44:  8241 
    Google Scholar
  • 5b Yashin NV. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis  2006,  279 
    Google Scholar
  • 6a Averina EB. Yashin NV. Kuznetsova TS. Zefirov NS. Vestn. Mosk. Univer., Ser. 2: Khim.  2002,  43:  246 ; Chem. Abstr. 2002, 138, 254854
    Google Scholar
  • 6b Averina EB. Yashin NV. Shvorina EB. Grishin YuK. Kuznetsova TS. Vestn. Mosk. Univer., Ser. 2: Khim.  2005,  46:  314 ; Chem. Abstr. 2005, 145, 145989
    Google Scholar
  • 6c Yashin NV. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis  2006,  880 
    Google Scholar
  • 7a Matveeva ED. Podrugina TA. Tishkovskaja EV. Tomilova LG. Zefirov NS. Synlett  2003,  2321 
    Google Scholar
  • 7b Zefirov NS. Matveeva ED. ARKIVOC  2008,  (i):  1 
    Google Scholar
  • 7c Yashin NV. Villemson EV. Chemagin AV. Averina EB. Kabachnik MM. Kuznetsova TS. Synthesis  2008,  464 
    Google Scholar
  • 8 Regitz M. Weber B. Eckstein U. Liebigs Ann. Chem.  1979,  1002 
    CrossrefGoogle Scholar
  • 9a Sifniades S. J. Org. Chem.  1975,  40:  3562 
    Google Scholar
  • 9b Neimysheva AA. Muratov SS. Smirnov EV. Solntseva LM. Zh. Obshch. Khim.  1976,  46:  940 ; Chem. Abstr. 1976, 85, 712
    Google Scholar
  • 9c Takeuchi Y. Ogura H. Kanada A. Koizumi T. J. Org. Chem.  1992,  57:  2196 
    Google Scholar
  • 10 Charette AB. Wurz RP. Ollevier T. J. Org. Chem.  2000,  65:  9252 
    CrossrefPubMedGoogle Scholar
  • 11a Charette AB. Wurz RP. J. Mol. Catal. A: Chem.  2003,  196:  83 
    Google Scholar
  • 11b Titanyuk ID. Beletskaya IP. Peregudov AS. Osipov SN. J. Fluorine Chem.  2007,  128:  723 
    Google Scholar
  • 12 Charette AB. Wurz RP. Ollevier T. Helv. Chim. Acta  2002,  85:  4468 
    CrossrefGoogle Scholar
  • 13 Perrin DD. Armarego WLF. Purification of Laboratory Chemicals   Pergamon; Oxford: 1966.  p.362 
    Google Scholar
  • 14 Calogeropoulou T. Hammond GB. Wiemer DF. J. Org. Chem.  1987,  52:  4185 
    CrossrefGoogle Scholar
  • 15 Binger P. Brinkmann A. Wedemann P. Synthesis  2002,  1344 
    Article in Thieme ConnectGoogle Scholar
  • 16 Zefirov NS. Kozhushkov SI. Kuznetsova TS. Kokoreva OV. Lukin KA. Trach SS. Ugrak BI. J. Am. Chem. Soc.  1990,  112:  7702 
    Google Scholar
  • 17 Sternberg E. Binger P. Tetrahedron Lett.  1985,  26:  301 
    CrossrefGoogle Scholar
  • 18 Cripps HN. Williams JK. Sharkey WH. J. Am. Chem. Soc.  1959,  81:  2723 
    CrossrefGoogle Scholar
  • 19 Beckhaus H.-D. Ruechardt C. Kozhushkov SI. Belov VN. Verevkin SP. de Meijere A. J. Am. Chem. Soc.  1995,  117:  11854 
    CrossrefGoogle Scholar
  • 20 Christol H. Cristau H.-J. Soleiman M. Synthesis  1975,  736 
    Article in Thieme ConnectGoogle Scholar
  • 21 Neimysheva AA. Muratov SS. Smirnov EV. Solntseva LM. Zh. Obshch. Khim.  1976,  46:  940 ; Chem. Abstr. 1976, 85, 712
    Google Scholar