Abstract
Hydrolysis of 2-alkoxyalk-2-enals with equimolar amount of water (in an organic solvent) and with an excess of water has been studied with the aim of synthesizing 2-oxopropanal (methylglyoxal). 2-Oxopropanal obtained in an excess of water exists in the hydrate from. In organic solvents, the cyclic trimer of 2-oxopropanal, 2,4,6-triacetyl-1,3,5-trioxane, predominates (NMR data).
References
M. F. Shostakovskii, N. A. Keiko, and A. Kh. Filippova,Izv. Akad. Nauk SSSR, Ser. Khim., 1967, 392 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1967,16 (Engl. Transl.)].
L. G. Egyud and A. Szent-Gyorgyi,Science, 1968,160, 1140.
V. S. Alekseev and N. V. Alekseeva,Ukr. Biokhim. Zh., [Ukrainian Biochemical Journal], 1990,62, 13 (in Russian).
H. J. Sanders and A. W. Taff,Ind. Eng. Chem., 1954,46, 414.
G. Leoncini,Italian J. of Biochemistry, 1979,28, 285.
M. Fedoronko, M. Petrusova, and I. Tvaroska,Carbohydrate Rev., 1983,115, 85.
Sho-Chow Woo and Sze-Tseng Chang,Trans. Faraday Soc., 1945,41, 157.
N. A. Keiko, T. N. Musorina, Yu. L. Frolov, A. M. Shulunova, Yu. A. Chuvashev, and M. G. Voronkov,Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 1993 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981,30 (Engl. Transl.)].
J. Furukawa, and T. Saegusa,Polymerization of Aldehydes and Oxides, Wiley, New York, 1963.
J. L. Jangnichel and C. A. Reilly,J. Mol. Spectr., 1965,16, 135.
T. N. Mamashvili, N. A. Keiko and M. G. Voronkov,Zh. Org. Khim., 1995,31, 429 [Russ. J. Org. Chem., 1995,31 (Engl. Transl.)].
N. A. Keiko and M. F. Shostakovskii,Dokl. Akad. Nauk SSSR, 1965,162, 362, [Dokl. Chem., 1965 (Engl. Transl.)].
N. A. Keiko, M. F. Shostakovskii, and A. P. Chichkarev,Izv. Akad. Nauk SSSR, Ser. Khim., 1967, 2351 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 196716 (Engl. Transl.)].
Houben-Weyl,Methoden der Organische Chemie, Stuttgart, 1955,3, 2; 75.
Beilstein Handbuch der Organische Chemie, Berlin, 1942, 1,EII, s. 822.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2547–2549, December, 1998.
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Mamashvili, T.N., Keiko, N.A., Sarapulova, G.I. et al. Hydrolysis of 2-alkoxyalk-2-enals. Russ Chem Bull 47, 2465–2467 (1998). https://doi.org/10.1007/BF02641556
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DOI: https://doi.org/10.1007/BF02641556