Chemistry of Polyhalogenated Nitrobutadienes, Part 7: A Novel Synthetic Access to Chlorinated Nitrile Oxides

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

Reaction of gem-dichloronitroalkenes with base leads to the formation of chlorinated nitrile oxides, probably via a cyclic intermediate. The 1,3-dipoles can be trapped with alkenes to give dihydroisoxazoles with a chlorinated side chain in 3-position. This novel synthetic method is fairly general.

References

• 1 Kaberdin RV. Potkin VI. Zapol’skii VA. Russ. Chem. Rev.  1997,  10:  827 
  Google Scholar
• 2 Zapol’skii VA. Namyslo JC. Adam AEW. Kaufmann DE. Heterocycles  2004,  63:  1281 
  CrossrefGoogle Scholar
• 3 Zapol’skii VA. Namyslo JC. Gjikaj M. Kaufmann DE. Synlett  2007,  1507 
  Article in Thieme ConnectGoogle Scholar
• 4 Vashkevich EV. Potkin VI. Kozlov NG. Russ. J. Org. Chem.  2005,  41:  739 
  CrossrefGoogle Scholar
• 5 Ol’dekop YS. Kaberdin RV. Potkin VI. Shingel IA. J. Org. Chem. USSR (Engl. Transl.)  1979,  15:  39 
  Google Scholar
• 6 Zapol’skii VA. Nutz E. Namyslo JC. Adam AEW. Kaufmann DE. Synthesis  2006,  2927 
  Article in Thieme ConnectGoogle Scholar
• 7 Litvinovskaya RP. Khripach VA. Russ. Chem. Rev.  2001,  70:  405 
  CrossrefGoogle Scholar
• 8 Melo T. Curr. Org. Chem.  2005,  9:  925 
  CrossrefGoogle Scholar
• 9 Caldirola P. Ciancaglione M. De Amici M. De Micheli C. Tetrahedron Lett.  1986,  27:  4647 
  CrossrefGoogle Scholar
• 10a Ponzio G. Gazz. Chim. Ital.  1936,  66:  115 
  Google Scholar
• 10b Ponzio G. Gazz. Chim. Ital.  1941,  71:  693 
  Google Scholar
• 11 Torssel KBG. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis   VCH; Weinheim: 1988. 
  Google Scholar
• 12a Jäger V. Colinas PA. In The Chemistry of Heterocyclic Compounds   Vol. 59:  Padwa A. Pearson WH. Wiley; New York: 2002.  p.361 
  Google Scholar
• 12b Kislyi VP. Laikhter AL. Ugrak BI. Semenov VV. Russ. Chem. Bull.  1994,  43:  98 
  Google Scholar
• 12c Barrett D. Bentley PD. Perrior TR. Synth. Commun.  1996,  26:  3401 
  Google Scholar
• 13a Kanemasa S. In Science of Synthesis   Vol. 19:  Murahashi S.-I. Thieme; Stuttgart: 2004.  p.17 
  Google Scholar
• 13b Belen’kii LI. Nitrile Oxides, In Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis   2nd ed.:  Feuer H. Wiley; Hoboken: 2008.  p.1 
  Google Scholar
• 14 Huisgen R. Mack W. Anneser E. Angew. Chem.  1961,  73:  656 
  Google Scholar
• 15 Mukaiyama T. Hoshino T. J. Am. Chem. Soc.  1960,  82:  5339 
  CrossrefGoogle Scholar
• 16 Curran DP. Fenck CJ. J. Am. Chem. Soc.  1985,  107:  6023 
  CrossrefGoogle Scholar
• 17 Gasparrini F. Giovannoli M. Misiti D. Natile G. Palmieri G. Maresca L. J. Am. Chem. Soc.  1993,  115:  4401 
  CrossrefGoogle Scholar
• 18 Grant RD. Pinhey JT. Aust. J. Chem.  1984,  37:  1231 
  CrossrefGoogle Scholar
• 19a Barr L. Lincoln SF. Easton CJ. Chem. Eur. J.  2006,  12:  8571 
  Google Scholar
• 19b Meyer AG. Easton CJ. Lincoln SF. Simpson GW. J. Org. Chem.  1998,  63:  9069 
  Google Scholar
• 20a Kanemasa S. Okuda K. Yamamoto H. Kaga S. Tetrahedron Lett.  1997,  38:  4095 
  Google Scholar
• 20b Alguacil R. Fariña F. Martín MV. Tetrahedron  1996,  52:  3457 
  Google Scholar
• 21 Bagatti M. Rastelli A. Burdisso M. Gandolfi R. J. Phys. Org. Chem.  1992,  5:  819 
  CrossrefGoogle Scholar
• 22 Namboothiri INN. Rastogi N. Ganguly B. Mobin SM. Cojocaru M. Tetrahedron  2004,  60:  1453 
  CrossrefGoogle Scholar
• 23 Preparation: Zapol’skii VA. Potkin VI. Kaberdin RV. Russ. J. Org. Chem.  1994,  30:  1435 
  Google Scholar
• 24 Preparation: Zapol’skii VA. Namyslo JC. Blaschkowski B. Kaufmann DE. Synlett  2006,  3464 
  Article in Thieme ConnectGoogle Scholar
• 25 Halling K. Thomsen I. Torssell KBG. Liebigs Ann. Chem.  1989,  985 
  CrossrefGoogle Scholar
• 26 Stevens RV. Polniaszek RP. Tetrahedron  1983,  39:  743 
  CrossrefGoogle Scholar
• 27 Preparation: Meyer Chr. Zapol’skii VA. Adam AEW. Kaufmann DE. Synthesis  2008,  2575 
  Article in Thieme ConnectGoogle Scholar
• 28 Preparation: Ol’dekop YA. Kaberdin RV. J. Org. Chem. USSR (Engl. Transl.)  1976,  12:  1986 
  Google Scholar