Abstract
[2+3] Cycloaddition of 3-nitropropene-1 with C,C,N-triphenylnitrone leads to a mixture of 5-nitromethyl-2,3,3-triphenylisoxazolidine and 5-methyl-4-nitro-2,3,3-triphenylisoxazolidine. The results obtained can be explained assuming that 3-nitropropene-1 isomerizes to 1-nitropropene-1 under reaction conditions.
Similar content being viewed by others
References
R. Jasinski and A. Baranski, Polish J. Chem., 80(No.9) (2006).
A. Baranski and R. Jasinski, Khim. Geterotsikl. Soed., 1670 (2001). [Chem. Heterocycl. Comp., 37, 1518 (2001)].
A. Baranski, Khim. Geterotsikl. Soed., 840 (2000). [Chem. Heterocycl. Comp., 36, 738 (2000)].
R. Jasinski, A. Ciezkowska, A. Lyubimtsev, and A. Baranski, Khim. Geterotsikl. Soed., 243 (2004). [Chem. Heterocycl. Comp., 40, 206 (2004)].
I. A. Motorina and L. A. Sviridova, Khim. Geterotsikl. Soed., 829 (1992). [Chem. Heterocycl. Comp., 28, 689 (1992)].
P. N. Confalone and E. M. Huie, Org. React., 36, 46 (1988).
A. Baranski, G. A. Shvekhgeimer, and N. I. Kirillova, Polish J. Chem., 54, 23 (1980).
V. Yu. Baskov, T. Urbanski, M. Witanowski, and L. Stefaniak, Tetrahedron., 20, 1519 (1964).
G. Hesse and V. Jäger, Liebigs Ann. Chem., 740, 85 (1970).
R. Sustmann R., Tetrahedron Lett., 717 (1971).
I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, Chichester, 1976.
V. Meyer and P. Askenazy, Ber., 25, 1701 (1892).
M. Stadinger, M. Miescher, Helv. Chim. Acta., 2, 568 (1919).
G. D. Buckley, C. W. Scaife, J. Chem. Soc., 1417 (1947).
Author information
Authors and Affiliations
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1545–1548, October, 2006.
Rights and permissions
About this article
Cite this article
Jasinski, R., Kwiatkowska, M. & Baranski, A. Synthesis and properties of azoles and their derivatives. 57. Unexpected results of 3-nitropropene-1 [2+3] cycloaddition to C,C,N-triphenylnitrone. Chem Heterocycl Compd 42, 1334–1337 (2006). https://doi.org/10.1007/s10593-006-0244-6
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-006-0244-6