Beilstein J. Org. Chem.2021,17, 273–282, doi:10.3762/bjoc.17.26
-quinones. A study of their monoreduced semiquinone derivatives reveal that the spin density is delocalized across the whole molecule, including peripheral fragments. The first stable o-quinone derivative bearing an annulated thiete heterocycle has been isolated and characterized.
Keywords: dioxolene
ligand; 1,3-dithiole; ditopic ligand; o-quinone; thiete; Introduction
There are a number of methods which may be used for the synthesis of new o-quinones in order to vary their redox properties and coordination abilities. The key features of o-quinones are redox activity as well as chelating
was not the only product of the reaction of 4 with acetylacetone gem-dithiolate 5d. The final mixture also contained o-quinone 7 with attached four-membered thiete ring (Scheme 1 and Scheme 2). The formation of the latter was surprising for us.
The X-ray study of 6d revealed that the six-membered o
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Graphical Abstract
Scheme 1:
Synthetic pathways for the preparation of o-quinone derivatives with annulated 1,3-dithiole ring.