Abstract
Hydroalumination-iodination of alkyne-1,4-diols of different structure showed that with increasing number of substituents at the C-OH group the amount of β-iodo-substituted products with respect to this group increased. In the case of symmetric secondary 1,4-diols the reaction results in a 1: 1 mixture of stereoisomeric iodoalkenediols, and in the case of phenyl substituents the reaction proceeds regio- and stereoselectively to give an alkenediol iodine atom in the β-position to phenyl group.
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Corey, E.J., Katzenellenbogen, J.A., and Posner, G.H., J. Am. Chem. Soc., 1967, vol. 89, no. 16, p. 4245.
Zakharkin, L.I., Vinnikova, M.I., and Gavrilenko, V.V., Russ. Chem. Bull., 1987, no. 3, p. 582.
Corey, E.J., Katzenellenbogen, J.A., Gilman, N.W., Roman, S.A., and Erickson, B.W., J. Am. Chem. Soc., 1968, vol. 90, p. 5618.
Corey, E.J. and Yamamoto, H., J. Am. Chem. Soc., 1970, vol. 92, p. 6636.
Corey, E.J. and Yamamoto, H., J. Am. Chem. Soc., 1970, vol. 92, p. 6637.
Khrimyan, A.P., Gharibian, O.A., Streinz, L., Wimmer, Z., Romanuk, M., and Badanyan, S.O., Collect. Czech. Chem. Commun., 1989, vol. 54, no. 11, p. 3284.
Khrimyan, A.P., Gharibyan, O.A., Panosyan, G.A., Mailyan, N.Sh., Kinoyan, F.S., Makaryan, G.M., and Badanyan, Sh.O., Zh. Org. Khim., 1993, vol. 29, no. 12, p. 2351.
Day, A.C. and Witing, W.C., J. Chem. Soc. (B), 1967, p. 991.
Gharibyan, O.A., Makaryan, G.M., Kinoyan, F.S., Chobanyan, Zh.A., Khim. Zh. Arm., 2009, vol. 62, nos. 3–4, p. 369
Gharibyan, O.A., Makaryan, G.M., Marandyan, A.A., Sarkisova, O.V., Kazaryan, N.S., Ogannisyan, M.R., and Chobanyan, Zh.A., Khim. Zh. Arm., 2011, vol. 64, no. 1, p. 91.
Vlasov, V.M., Vasil’eva, A.A., and Semenova, U.F., Zh. Org. Khim., 1965, vol. 2, no. 4, p. 595
Henbest, H.B., Jones, E.R.H., and Walls, I.M.S., J. Chem. Soc., 1950, p. 3646.
Yasunobu, T. and Takesi, M., J. Chem. Soc. Japan. Pure Chem. Sect., 1963, vol. 84, no. 2, p. 145.
France Patent no. 2108342, 1971.
Fiesselmann, H. and Sasse, K., Chem. Ber., 1956, vol. 90, no. 7, p. 1775.
Vlasov, V.M., Kuznetsova, T.S., and Derigladov, N.M., Zh. Org. Khim., 1967, vol. 3, no. 2, p. 277.
Veliev, M.G. and Guseinov, M.M., Synthesis, 1980, no. 6, p. 461.
Zil’kind, Yu.S. and Gverdtsiteli, I.M., Zh. Obshch. Khim., 1939, vol. 9, no. 11, p. 971.
Levina, R.Ya. and Sharabarov, Yu.S., Dokl. Akad. Nauk SSSR, 1952, vol.84, p. 709.
Zil’kind, Yu.S. and Ivanov, R.P., Zh. Obshch. Khim., 1941, vol. 11, no. 10, p. 803.
Malenok, N.M. and Sologub, I.V., Zh. Obshch. Khim., 1955, vol. 25, no. 10, p. 2223.
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Original Russian Text © H.A. Gharibyan, G.M. Makaryan, M.R. Hovhannisyan, F.S. Kinoyan, Zh.A. Chobanyan, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 3, pp. 399–406.
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Gharibyan, H.A., Makaryan, G.M., Hovhannisyan, M.R. et al. Some special features of hydroalumination-iodination of alkyne-1,4-diols. Russ J Gen Chem 84, 457–464 (2014). https://doi.org/10.1134/S1070363214030086
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DOI: https://doi.org/10.1134/S1070363214030086