Subscribe to RSS
DOI: 10.1055/s-2004-834940
Three-Component Reactions of Halogenotrinitromethanes with Alkenes
Publication History
Publication Date:
01 December 2004 (online)
Abstract
Three-component one-pot reactions of bromotrinitromethane with bicyclobutylidene and methylenecyclobutanes provide a simple route to halogen-substituted isoxazolidines of mixed composition. With these same olefins, iodotrinitromethane gives adducts which decomposed rapidly to yield the corresponding isoxazolines. Reaction of bromotrinitromethane and bicyclobutylidene with electron-deficient alkenes produced isoxazolidines together with bromotrinitroalkanes as side products.
Key words
multi-component reaction - cycloaddition - heterocycles - small ring systems - polynitro compounds
-
1a
Altukhov KV.Perekalin VV. Usp. Khim. 1976, 45: 2050 ; Chem. Abstr. 1977, 86, 71774s -
1b
Fridman AL.Surkov VD.Novikov SS. Usp. Khim. 1980, 49: 2159 ; Chem. Abstr. 1981, 94, 156194t - 2
Averina EB.Ivanova OA.Grishin YK.Kuznetsova TS.Zefirov NS. Russ. J. Org. Chem. 2000, 36: 1562 -
3a
Budynina EM.Ivanova OA.Averina EB.Grishin YK.Kuznetsova TS.Zefirov NS. Dokl. Chem. 2002, 387: 304 -
3b
Averina EB.Budynina EM.Ivanova OA.Grishin YK.Gerdov SM.Kuznetsova TS.Zefirov NS. Zh. Org. Khim. (Russ) 2004, 40: 186 - 5
Ivanova OA.Averina EB.Grishin YK.Kuznetsova TS.Korlyukov AA.Antipin MY.Zefirov NS. Dokl. Chem. 2002, 382: 21 - 6
Anspon HD. inventors; US Patent 3041379. ; Chem. Abstr. 1962, 57, 13618h -
7a
Hassan A.Wazeer MIM.Perzanowski HP.Ali SA. J. Chem. Soc., Perkin Trans. 2 1997, 411 -
7b
Lagodzinskaya GV. Zh. Struct. Khim. 1970, 11: 31 ; Chem. Abstr. 1970, 73, 9212k -
7c
Berg U.Butts CP.Eberson L.Hartshorn MP.Persson O. Acta Chem. Scand. 1998, 52: 761 - 8
Schmidt E.Schumacher R.Kuhlmann H. Chem. Ber. 1921, 54: 1483 - 9
Hantzsch V. Chem. Ber. 1906, 39: 2478 - 10
Cripps HN.Williams JK.Shakery WH. J. Am. Chem. Soc. 1959, 81: 2723
References
The scope of the stated method is restricted to nucleophilic and hindered olefins like tri- and tetrasubstituted alkyl or aryl cycloalkenes, which form nitronic esters in situ. For analogues see ref.3