Abstract
2,2-Bis(alkoxy-NNO-azoxy)propane-1,3-diols react with sulfonyl chlorides and trifluoromethanesulfonic anhydride in the presence of bases affording previously unknown methane-, trifluoromethane-, benzene and toluenesulfonates (sulfonic esters) of 2-bis(methoxy- and ethoxy-NNO-azoxy)propane-1,3-diols. The triflates are thermally less stable than mesylates, benzenesulfonates, and tosylates of the corresponding diols.
Similar content being viewed by others
References
Behrend, R. and Konig, E., Lieb. Ann., 1891, vol. 263, p. 175.
Traube, W., Lieb. Ann., 1898, vol. 300, p. 81.
Yandovskii, V.N., Gidaspov, B.V., and Tselinskii, I.V., Russ. Chem. Rev., 1980, vol. 49, p. 237.
Zlotin, S.G. and Luk’yanov, O.A., Russ. Chem. Rev., 1993, vol. 62, p. 143.
Hrabie, J.A. and Keefer, L.K., Chem. Rev., 2002, vol. 102, p. 1135.
Brand, J., Huhn, T., Groth, U., and Jochims, J.C., Chem. Eur. J., 2006, vol. 12, p. 499.
Granik, V.G. and Grigor’yev, N.B., Russ. Chem. Bull., vol. 51, p. 1375.
Lempert, D.B., Avdonin, V.V., and Nechiporenko, G.N., Russ. J. Appl. Chem., 1998, vol. 71, p. 47.
Zyuzin, I.N. and Lempert, D.B., Propellants, Explosives, Pyrotechnics, 2007, vol. 32, p. 42.
Yandovskii, V.N., Dobrodumova, E.Yu., and Tselinskii, I.V., Zh. Org. Khim., 1980, vol. 16, p. 933.
Zyuzin, I.N., Russ. Chem. Bull., 1985, vol. 34, p. 2433.
Marchenko, G.A., Mukhametzyanov, A.S., and Tselinskii, I.V., J. Org. Chem. USSR (Engl. Transl.), 1985, vol. 21, p. 1297.
Zyuzin, I.N., Golovina, N.I., Lempert, D.B., Nechiporenko, G.N., and Shilov, G.V., Russ. Chem. Bull., 2008, vol. 57, p. 632.
Zyuzin, I.N., Golovina, N.I., Lempert, D.B., and Shilov, G.V., Russ. Chem. Bull., 2010, vol. 59, p. 1925.
Zyuzin, I.N., Russ. J. Appl. Chem., 2009, vol. 82, p. 1799.
Zyuzin, I.N. and Lempert, D.B., Russ. Chem. Bull., 2009, vol. 58, p. 2173.
Zyuzin, I.N., Suponitsk, K.Yu., and Sheremetev, A.B., J. Heterocycl. Chem., 2012, vol. 49, p. 561.
Marchenko, G.A., Mukhametzyanov, A.S., Tselinskii, I.V., and Ermoshkin, I.V., J. Org. Chem. USSR (Engl. Transl.), 1985, vol. 21, p. 1300.
Zyuzin, I.N., Golovina, N.I., and Shilov, G.V., Russ. J. Org. Chem., 2010, vol. 46, p. 1085.
Jones, D.N., Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, Press, 1979, vol. 3, 1338 p.
Redkin, Yu.A., Marchenko, G.A., Punegova, L.N., Stepanov, G.S., and Tselinskii, I.V., Russ. J. Org. Chem. USSR (Engl. Transl.), 1988, vol. 24, p. 441.
Zyuzin, I.N., Russ. J. Org. Chem., 2013, vol. 49, p. 536.
Zyuzin, I.N., Russ. J. Org. Chem., 2013, vol. 49, p. 678.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © I.N. Zyuzin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 5, pp. 646–649.
Rights and permissions
About this article
Cite this article
Zyuzin, I.N. 2,2-Bis(methoxy- and ethoxy-NNO-azoxy)propane-1,3-diol sulfonates. Russ J Org Chem 50, 631–634 (2014). https://doi.org/10.1134/S1070428014050030
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428014050030