QUANTUM-CHEMICAL ANALYSIS OF THE ALGAR–FLYNN–OYAMADA REACTION MECHANISM

Authors

  • И. Э. Сердюк Scientific-Research Institute of Chemistry, V. N. Karazin Kharkiv National University; University of Gdańsk
  • А. Д. Рошаль Scientific-Research Institute of Chemistry, V. N. Karazin Kharkiv National University
  • Е. Блажейовски University of Gdańsk

DOI:

https://doi.org/10.1007/1538

Keywords:

chalcone, epoxychalcone, flavonol, Algar-Flynn-Oyamada reaction, reaction mechanism

Abstract

This work is devoted to improving the understanding of Algar–Flynn–Oyamada reaction mechanism and the analysis of factors that affect the formation of flavonols. The calculation of thermodynamic parameters for the key reaction steps pointed to a mechanism involving chalcone epoxides as intermediates. A correlation was identified between the nucleophilicity of oxygen atom at  position 2' of epoxide anions and the yields of flavonols. An increased charge at the nucleophilic center was shown to reduce the effectiveness of β-cyclization of epoxide anions.

How to Cite
Serdiuk, I. E.; Roshal, A. D.; Błażejowski, J. Chem. Heterocycl. Compd. 2014, 50, 393. [Khim. Geterotsikl. Soedin. 2014, 431.]

For this article in the English edition see DOI 10.1007/s10593-014-1487-2

Author Biographies

И. Э. Сердюк, Scientific-Research Institute of Chemistry, V. N. Karazin Kharkiv National University; University of Gdańsk

Илья Эдуардович Сердюк

отдел физико-органической химии, аспирант

А. Д. Рошаль, Scientific-Research Institute of Chemistry, V. N. Karazin Kharkiv National University

Александр Давидович Рошаль

отдел физико-органической химии, старший научный сотрудник, к.х.н., Dr. hab.

Е. Блажейовски, University of Gdańsk

Ежи Блажейовски

Зав. кафедрой физической химии, профессор, Dr.hab. inz.

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Published

2014-03-17

Issue

No. 3 (2014)

Section

Original Papers