Unusual Reaction of Sodium 1,6-Dioxo-2,4-alkadiene-3,4-diolates under Acid Hydrolysis Conditions

Russian Journal of General Chemistry - Tập 88 - Trang 2039-2043 - 2018
P. P. Mukovoz1, P. A. Slepukhin2,3, I. N. Ganebnykh2,3, O. S. El’tsov3, E. A. Danilova4
1All-Russian Research Institute of Phytopathology, Bol’shiye Vyazemy, Moscow oblast’, Russia
2Postovskii Institute of Organic Synthesis, Yekaterinburg, Russia
3Ural Federal University named after the First President of Russia B. N. Yeltsin, Yekaterinburg, Russia
4Ivanovo State University of Chemistry and Technology, Ivanovo, Russia

Tóm tắt

The reaction of sodium 1,6-dioxo-2,4-alkadiene-3,4-diolates with HCl solution afforded unexpected hydrolysis products, namely (2Z)-2-hydroxy-4-oxobut-2-enoic (2,4-dioxobutanoic) acid esters. The structural features of the synthesized compounds were discussed on the basis of IR, 1H NMR spectroscopy, mass spectrometry and X-ray diffraction analysis data.

Tài liệu tham khảo

Mukovoz, P.P., Koz’minykh, V.O., Gorbunova, A.V., Slepukhin, P.A., El’tsov, O.S., Ganebnykh, I.N., and Kuzmin, A.V., Russ. J. Gen. Chem., 2016, vol. 86, no. 11, p. 2427. doi 10.1134/S1070363216110050 Mukovoz, P.P., Koz’minykh, V.O., and Tarasova, V.A., Russ. J. Org. Chem., 2015, vol. 50, no. 11, p. 1687. doi 10.1134/S1070428014110244 Mukovoz, P.P., Koz’minykh, V.O., and Dvorskaya, O.N., Izv. Vuzov. Ser. Khim. i Khim. Tekhnol., 2011, vol. 54, no. 5, p.96. Tarasova, V.A., Mukovoz, P.P., and Koz’minykh, V.O., Vestn. YuUGU. Ser. Khim., 2014, vol. 6, no. 3, p.11. Mukovoz, P.P., Candidate Dissert. (Chem. Sci.), Yaroslavl, 2010. Mukovoz, P.P., Andreeva, V.A., Koz’minykh, V.O., El’tsov, O.S., Ganebnykh, I.N., and Koz’minykh, E.N., Russ. J. Org. Chem., 2016, vol. 52, no. 1, p. 1. doi 10.1134/S1070428016010012 Karmanova, O.G., Koz’minykh, V.O., and Mukovoz, P.P., Bash. Khim. Zh., 2012, vol. 19, no. 2, p.82. Koz’minykh, V.O., Goncharov, V.I., and Koz’minykh, E.N., Vestn. Orenburgsk. Gos. Univ., 2007, no. 5, p.138. Koz’minykh, V.O., Goncharov, V.I., Koz’minykh, E.N., and Nozdrin, I.N., Vestn. Orenburgsk. Gos. Univ., 2007, no. 3, p.112. Stachel, H.-D., Lieb. Ann. Chem., 1965, no. 689, p. 118. doi 10.1002/jlac.19656890110 Aliev, Z.G., Shurov, S.N., Nekrasov, D.D., Podvintsev, I.B., and Atovmyan, L.O., J. Struct. Chem., 2000, vol. 41, no. 6, p. 1041. doi 10.1023/A:1010323410035 Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Cryst. (A), 2009, vol. 42, p. 339. doi 10.1107/S0021889808042726 Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. doi 10.1107/S0108767307043930