Synthesis of carbomethoxymethylidene cyclopentenedione derivatives based on oxidative cleavage reactions of the allylic double bond 2-allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)-cyclopent-4-en-1,3-dione

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Abstract

The reactions of oxidative cleavage of the allyl double bond of 2-allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)-cyclopent-4-ene-1,3-dione in the systems OsO4–NaIO4 and KMnO4–Et3BnN+Cl- were studied. It was shown that the intermediate aldehyde formed at the stage of periodate cleavage of the indicated 2-allylcyclopentene-1,3-dione was oxidized by the Jones reagent and, with subsequent elimination of HCl, was converted into the target 2-carbomethoxymethylidenecyclopent-4-ene-1,3-dione. In an alternative approach, permanganate oxidation of the basic 2-allylcyclopentene-1,3-dione leads to the corresponding diol in moderate yield.

About the authors

V. A. Egorov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Email: fangim@anrb.ru
ORCID iD: 0000-0001-9710-265X
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

L. S. Khasanova

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Email: fangim@anrb.ru
ORCID iD: 0000-0002-7183-4200
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

F. A. Gimalova

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Author for correspondence.
Email: fangim@anrb.ru
ORCID iD: 0000-0002-5176-1227
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

M. S. Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Email: fangim@anrb.ru
ORCID iD: 0000-0002-0269-7484
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

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