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JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2021 Volume 31, Issue 6, Pages 824–826 (Mi mendc1055)

This article is cited in 4 papers

Communications

Oxidation step in the preparation of benzocamalexin: The crystallographic evidence

Y. Stremskia, A. I. Ahmedovab, A. Dolegac, S. Statkova-Abeghea, D. Kirkovad

a Department of Chemistry, University of Plovdiv 'Paisii Hilendarski', Plovdiv, Bulgaria
b Faculty of Chemistry, University of Sofia, Sofia, Bulgaria
c Faculty of Chemistry, University of Gdansk, Gdansk, Poland
d Chemistry of Tobacco and Tobacco Smoke, Tobacco and Tobacco Products Institute BG, Plovdiv, Bulgaria

Abstract: The study of oxidation step in the preparation of benzocamalexin by the α-amidoalkylation–oxidation sequence revealed the formation of perchloro-1,2-phenylene dibenzoate as the product of transformation of tetrachloro- 1,2-benzoquinone applied as the oxidant. The structures of benzocamalexin and perchloro-1,2-phenylene dibenzoate were confirmed by X-ray diffraction analysis. The extraction step in the final isolation of benzocamalexin is supposed to be crucial for the complete transformation of mono- and di- acylated perchloropyrocatechol.

Keywords: benzocamalexin, phytoalexins, α-amidoalkylation, crystal structures, o-chloranil.

Language: English

DOI: 10.1016/j.mencom.2021.11.018



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