Abstract
Iminiodifluoromethanides generated from difluorocarbene and benzophenone or fluorenone imines enter into reaction of 1,3-cycloaddition with electron-deficient alkenes to furnish pyrrolidone derivatives. The generation of iminiodifluoromethanides from alkyl N-benzhydrylidene glycinates in the presence of dipolarophiles is liable to complication by a concurrent proton shift in the initial imine giving NH-azomethine ylide also capable of 1,3-dipolar cycloaddition resulting in a side product of pyrrolidone series. The use of active lead instead of lead powder as reductant for dibromodifluoromethane in generation of difluorocarbene permits suppressing formation of the side products in these reactions.
Similar content being viewed by others
REFERENCES
Khlebnikov, A.F., Novikov, M.S., Kostikov, R.R., Adv. Heterocycl. Chem., 1996, vol. 65, pp. 93-233.
Khlebnikov, A.F. and Kostikov R.R., Izvestiya Akad. Nauk, Seriya Khim., 1993, vol. 42, no. 4, pp. 646-654.
Khlebnikov, A.F., Novikov, M.S., and Kosti-kov, R.R.,Ros. Khim. Zh., 1999, vol. 43, no. 1, pp. 70-79.
Novikov, M.S., Khlebnikov, A.F., Besedina, O.V., and Kostikov, R.R., Tetrahedron Lett., 2001, vol. 42, pp. 4187-4190.
Romashin, Yu.N., Liu, M.T.H., Nijjar, S.S., and Attanasi, O.A., Chem. Commun., 2000, pp. 1147-1148.
Romashin, Yu.N., Liu, M.T.H., and Bonneau, R., Chem. Commun., 1999, pp. 447-448.
Romashin, Yu.N., Liu, M.T.H., Ma, W., and Moss, R.A., Tetrahedron Lett., 1999, vol. 40, pp. 7163-7165.
Novikov, M.S., Khlebnikov, A.F., Masalev, A.E., and Kostikov, R.R., Tetrahedron Lett., 1997, vol. 38, pp.4187-4190.
Novikov, M.S., Khlebnikov, A.F., Sidorina, E.S., and Kostikov, R.R., J. Fluorine Chem., 1998, vol. 90, pp. 117-119.
Novikov, M.S., Khlebnikov, A.F., Sidorina, E.S., and Kostikov, R.R., J. Chem. Soc., Perkin. Trans. I, 2000, no.2, pp. 231-237.
Novikov, M.S., Khlebnikov, A.F., Krebs, A., and Kostikov, R.R., Eur. J. Org. Chem., 1998, no. 2, pp. 133-137.
Khlebnikov, A.F. and Kostikov, R.R., Zh. Org. Khim., 1992, vol. 28, no. 3, pp. 482-488.
Khlebnikov, A.F., Nikiforova, T.Yu., and Kostikov, R.R., Zh. Org. Khim., 1996, vol. 32, no. 5, pp. 746-761.
Khlebnikov, A.F., Novikov, M.S., Nikiforova, T.Yu., and Kostikov, R.R., Zh. Org. Khim., 1999, vol. 35, no. 1, pp. 98-105.
Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Mendeleev Commun., 1997, no. 4, pp. 145-147.
Khlebnikov, A.F., Novikov, M.S., Khlebnikov, V.A., and Kostikov, R.R., Zh. Org. Khim., 2001, vol. 37, no. 4, pp. 542-547.
Fritz, H.P. and Kornrumpf, W.Z.,Z. Naturforsch., 1981, vol. 36b, pp. 135-1380.
Novikov, M.S., Khlebnikov, A.F., Sidorina, E.S., Masalev, A.E., Kopf, Yu., and Kostikov, R.R.,Zh. Org. Khim., 2002, vol. 38, no. 5, pp. 710-719.
Grigg, R., Chem. Soc. Rev., 1987, vol. 16, pp. 89-121.
.Moretti, I., Synthesis, 1974, no. 1, p. 141.
Dai, W., Srinivasan, R., and Katzenellenbogen, J.A., J. Org. Chem., 1989, vol. 54, no. 9, pp. 2204-2208.
Ingold, C.K. and Wilson, C.L., J. Chem. Soc., 1933, pp. 1493-1505.
O'Donnell, M.J. and Polt, R.L., J. Org. Chem., 1982, vol. 47, no. 13, pp. 2663-2666.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Novikov, M.S., Khlebnikov, A.F. & Kostikov, R.R. 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from Ketimines and Difluorocarbene to Symmetrically Substituted Olefins. Russian Journal of Organic Chemistry 38, 1647–1654 (2002). https://doi.org/10.1023/A:1022518319349
Issue Date:
DOI: https://doi.org/10.1023/A:1022518319349