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

S. Yu Panshina, O. V. Ponomarenko, A. A. Bakibaev, V. S. Sidelnikov, D. A. Kurgachev, V. S. Malkov, A. I. Khlebnikov, A. K. Tashenov

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)140-147
Number of pages8
JournalRussian Chemical Bulletin
Volume70
Issue number1
DOIs
Publication statusPublished - Jan 2021

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

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