A study of products of tetrakis(hydroxymethyl)glycoluril dehydroxymethylation in aqueous solutions


Panshina S.Y. Ponomarenko O.V. Bakibaev A.A. Sidelnikov V.S. Kurgachev D.A. Malkov V.S. Khlebnikov A.I. Tashenov A.K.
January 2021Springer

Russian Chemical Bulletin
2021#70Issue 1140 - 147 pp.

It was found that tetrakis(hydroxymethyl)glycoluril is unstable in aqueous solutions and undergoes stepwise dehydroxymethylation. The products of this process were identified by HPLC, 1D and 2D NMR spectroscopy. The main product of hydrolytic degradation at room temperature is tris(hydroxymethyl)glycoluril, which may be conditioned by the thermodynamic characteristics of the reaction. Further dehydroxymethylation to give di- and monohydroxymethyl glycoluril derivatives occurs under more severe conditions.

COSY , dehydroxymethylation , HMBC , HPLC , NMR , quantum chemical calculations , tetrakis(hydroxymethyl)glycoluril , tris(hydroxymethyl)glycoluril

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Kizhner Research Center, National Research Tomsk Polytechnic University, 30 Lenina prosp., Tomsk, 634050, Russian Federation
Faculty of Chemistry, National Research Tomsk State University, 36 Lenina prosp., Tomsk, 634050, Russian Federation
Faculty of Natural Sciences, L. N. Gumilyov Eurasian National University, 2 ul. Satbaeva, Nur-Sultan, 010000, Kazakhstan

Kizhner Research Center
Faculty of Chemistry
Faculty of Natural Sciences

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