Abstract
Diphenyl ditelluride reacts with 2,3-dichloroprop-1-ene in the system hydrazine hydrate-KOH along several parallel routes. Beside the nucleophilic chlorine substitution at the sp 3-hybridized carbon atom resulting in 2-chloro-3-phenyltellanylprop-1-ene the elimination of both chlorine atoms occurs affording a mixture of allene and methylacetylene. The reasons of the dual elimination reaction paths are considered.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Reutov, O.A., Kurts, A.L., and Butin, K.P., Organicheskaya khimiya. Ch. 1 (Organic Chemistry, Part 1), Moscow: BINOM. Laboratoriya znanii, 2004, p. 567.
Protective Groups in Organic Chemistry, McOmie, J., Ed., Springer, 1995.
Fukunaga, K. and Yamaguchi, H., Synthesis, 1981, vol. 11, p. 4292.
Nakayma, J., Machida, H., and Hoshino, M., Tetrahedron Lett., 1983, vol. 24, p. 3001.
Landini, D., Milesi, L., Quadri, M.L., and Rolla, F., J. Org. Chem., 1984, vol. 49, p. 152.
Russavskaya, N.V., Grabel’nykh, V.A., Levanova, E.P., Sukhomazova, E.N., Klyba, L.V., Zhanchipova, E.R., Albanov, A.I., Tatarinova, A.A., Elaev, A.V., Deryagina, E.N., Korchevin, N.A., and Trofimov, B.A., Russ. J. Org. Chem., 2006, vol. 42, p. 672.
Shimizu, T., Kawaguchi, M., Tsuchiya, T., Hirabayashi, K., and Kamigata, N., J. Org. Chem., 2005, vol. 70, p. 5036.
Zefirov, N.S. and Makhon’kov, D.I., Chem. Rev., 1982, vol. 82, p. 615.
Traven’, V.F., Organicheskaya khimiya (Organic Chemistry), Moscow: IKTs “Akadem-kniga,” 2006, vol. 1, p. 727.
Levanova, E.P., Grabel’nykh, V.A., Russavskaya, N.V., Klyba, L.V., Zhanchipova, E.R., Albanov, A.I., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen., Chem., 2009, vol. 79, p. 1097.
Levanova, E, P., Grabel’nykh, V.A., Russavskaya, N.V., Rozentsveig, I.B., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen., Chem., 2011, vol. 81, p. 611.
Levanova, E.P., Grabel’nykh, V.A., Russavskaya, N.V., Albanov, A.I., Elaev, A.V., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen., Chem., 2011, vol. 81, p. 1560.
Levanova, E.P., Vshivtsev, V.Yu., Grabel’nykh, V.A., E.N. Sukhomazova, N.V. Russavskaya, N.V., Albanov, A.I., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen., Chem., 2008, vol. 78, p. 1900.
Levanova, E.P., Grabel’nykh, V.A., Elaev, A.E., Russavskaya, N.V., Klyba, L.V., Albanov, A.I., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen., Chem., 2013, vol. 83, p. 1088.
Levanova, E.P., Grabel’nykh, V.A., Vakhrina, V.S., Russavskaya, N.V., Albanov, A.I., Klyba, L.V., Tarasova, O.A., Rozentsveig, I.B., and Korchevin, N.A., Russ. J. Gen., Chem., 2013, vol. 83, p. 1434.
Sadekov, I.D. and Minkin, V.I., Russ. Chem. Rev., 1995, vol. 64, p. 491.
Deryagina, E.N., Russavskaya, N.V., Papernaya, L.K., Levanova, E.P., Sukhomazova, E.N., and Korchevin, N.A., Russ. Chem. Bull., 2005, p. 2473.
Levanova, E.P., Grabelnykh, V.A., Elaev, A.V., Albanov, A.I., Klyba, L.V., Russavskaya, N.V., Tarasova, O.A., Rozentsveig, I.B., and Korchevin, N.A., J. Sulfur Chem., 2012, vol. 33, p. 505.
Sazonov, P.K., Artamkina, G.A., and Beletskaya, I.P., Russ. Chem. Rev., 2012, vol. 81, p. 317.
Granger, P., Chapelle, S., McWhinnie, W.R., and Al-Rubaie, A., J. Organometal. Chem., 1981, vol. 220, p. 149.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original English Text © E.P. Levanova, V.S. Vakhrina, V.A. Grabel’nykh, I.B. Rozentsveig, N.V. Russavskaya, A.I. Albanov, N.A. Korchevin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 2, pp. 186–189.
Rights and permissions
About this article
Cite this article
Levanova, E.P., Vakhrina, V.S., Grabel’nykh, V.A. et al. Reaction of diphenyl ditelluride with 2,3-dichloroprop-1-ene in the system hydrazine hydrate-KOH. Russ J Org Chem 50, 175–178 (2014). https://doi.org/10.1134/S1070428014020055
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428014020055