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Georg Thieme Verlag, Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 20(29), p. 2633-2637, 2018

DOI: 10.1055/s-0037-1611082

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Regioselective and Catalyst-Free Epoxidation of (E)-3-[3-(2-Hydroxyaryl)-3-oxoprop-1-en-1-yl]chromones

Journal article published in 2018 by Mohamed Hammadi, Oualid Talhi ORCID, Artur Silva ORCID, Rachid Ameraoui, Ridha Hassaine, Abdelghani Bouchama, Hasnia Abdeldjebar, Yamina Belmiloud, Meziane Brahimi, Filipe Paz, Khaldoun Bachari
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

The uncatalyzed reaction of hydrogen peroxide with (E)-3-[3-(2-hydroxyaryl)-3-oxoprop-1-en-1-yl]chromones resulted in a regio­selective epoxidation of the chromone intracyclic C(2)=C(3) double bond to afford unique isomeric (E)-7a-[3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]-1aH-oxireno[2,3-b]chromen-7(7aH)-ones in high yields. 2D NMR and single-crystal X-ray diffraction were used to elucidate the structures of the chromanone epoxides. Density functional theoretical studies demonstrated a high electrophilicity of the starting chromones.