Abstract
Low-temperature ozonolysis of 2-alkenyl-1,1-dichlorocyclopropanes under different conditions (O3/MeOH–CH2Cl2–NaOH, O3/MeOH or O3/CH2Cl2–AcOH with subsequent treatment with semicarbazide hydrochloride) afforded the corresponding carbonyl and carboxy derivatives at different ratios, depending on the substrate structure and workup procedure. Peroxide products of ozonolysis of 1,1-dichloro-2-ethenylcyclopropane [3-(2,2-dichlorocyclopropyl)-1,2,4-trioxolane and (2,2-dichlorocyclopropyl)(methoxy)methyl hydroperoxide] turned out to be more stable than those derived from 1,1-dichloro-2-ethenyl-2-methylcyclopropane and were isolated in the pure state.
Similar content being viewed by others
References
The Chemistry of Peroxides, Rappoport, Z., Ed., Chichester: Wiley, 2006, vol. 2, part1.
McGuire J., Bond G., and Haslam, P.J., Handbook of Chiral Chemicals, Ager, D., Ed., Boca Raton: Taylor & Francis, 2006, 2nd ed.
Hon, Y.-S. and Wong, Y.-C., Tetrahedron Lett., 2005, vol. 46, p. 1365.
Ishmuratov, G.Yu., Legostaeva, Yu.V., Botsman, L.P., and Tolstikov, G.A., Russ. J. Org. Chem., 2010, vol. 46, p. 1593.
Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Idrisova, Z.I., Muslukhov, R.R., Ishmuratova, N.M., and Tolstikov, G.A., Russ. J. Org. Chem., 2013, vol. 49, p. 1409.
Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Muslukhov, R.R., Ishmuratova, N.M., and Tolstikov, G.A., Russ. J. Org. Chem., 2014, vol. 50, p.928.
Raskil’dina, G.Z., Legostaeva, Yu.V., Garifullina, L.R., Sultanova, R.M., Ishmuratov, G.Yu., and Zlotskii, S.S., Dokl. Chem., 2015, vol. 462, p.127.
Raskil’dina, G.Z., Legostaeva, Yu.V., Garifullina, L.R., Sultanova, R.M., Ishmuratov, G.Yu., and Zlotskii, S.S., Lett. Org. Chem., 2016, vol. 13, p.652.
Raskil’dina, G.Z., Borisova, Yu.G., Yanybin, V.M., and Zlotskii, S.S., Pet. Chem., 2017, vol. 57, p.278.
Van Ornum, S.G., Champeau, R.M., and Pariza, R., Chem. Rev., 2006, vol. 106, p. 2990.
Willand-Charnley, R., Fisher, T.J., Johnson, B.M., and Dussault, P.H., Org. Lett., 2012, vol. 14, p. 2242.
Orchin, M. and Herrick, E.C., J. Org. Chem., 1959, vol. 24, p.139.
DeWeese, F.T., Minter, D.E., Nosovitch, J.T., and Rudel, M.G., Tetrahedron, 1986, vol. 42, p. 239.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © Yu.V. Legostaeva, L.R. Garifullina, G.Z. Raskil’dina, R.M. Sultanova, G.Yu. Ishmuratov, S.S. Zlotskii, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 3, pp. 373–377.
Rights and permissions
About this article
Cite this article
Legostaeva, Y.V., Garifullina, L.R., Raskil’dina, G.Z. et al. Low-Temperature Ozonolysis of 2-Alkenyl-1,1-dichlorocyclopropanes. Russ J Org Chem 54, 377–381 (2018). https://doi.org/10.1134/S1070428018030028
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428018030028