Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands

The fused 1,3-dithiole spacer seems to be very suitable for the functionalization of sterically hindered o-quinones with additional groups capable of coordination of metal ions and/or possessing a redox activity. An effective method for the synthesis of sterically hindered o-quinones containing 1,3-...

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Main Authors:	Sergey V. Norkov, Anton V. Cherkasov, Andrey S. Shavyrin, Maxim V. Arsenyev, Viacheslav A. Kuropatov, Vladimir K. Cherkasov
Format:	Article
Language:	English
Published:	Beilstein-Institut 2021-01-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	dioxolene ligand 1,3-dithiole ditopic ligand o-quinone thiete
Online Access:	https://doi.org/10.3762/bjoc.17.26

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spelling	doaj-c13151bfb47844738ba277e2e566a9212021-02-08T09:47:07ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-01-0117127328210.3762/bjoc.17.261860-5397-17-26Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligandsSergey V. Norkov0Anton V. Cherkasov1Andrey S. Shavyrin2Maxim V. Arsenyev3Viacheslav A. Kuropatov4Vladimir K. Cherkasov5G. A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Tropinina str. 49, Box-445, 603950 Nizhny Novgorod, RussiaG. A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Tropinina str. 49, Box-445, 603950 Nizhny Novgorod, RussiaG. A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Tropinina str. 49, Box-445, 603950 Nizhny Novgorod, RussiaG. A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Tropinina str. 49, Box-445, 603950 Nizhny Novgorod, RussiaG. A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Tropinina str. 49, Box-445, 603950 Nizhny Novgorod, RussiaG. A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Tropinina str. 49, Box-445, 603950 Nizhny Novgorod, RussiaThe fused 1,3-dithiole spacer seems to be very suitable for the functionalization of sterically hindered o-quinones with additional groups capable of coordination of metal ions and/or possessing a redox activity. An effective method for the synthesis of sterically hindered o-quinones containing 1,3-diketonate, dinitrile and p-quinone-methide functional groups at the periphery of the ligand has been developed. The novel compounds have rigid and conjugated structures and exhibit properties typical of o-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.https://doi.org/10.3762/bjoc.17.26dioxolene ligand1,3-dithioleditopic ligando-quinonethiete
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Sergey V. Norkov Anton V. Cherkasov Andrey S. Shavyrin Maxim V. Arsenyev Viacheslav A. Kuropatov Vladimir K. Cherkasov
spellingShingle	Sergey V. Norkov Anton V. Cherkasov Andrey S. Shavyrin Maxim V. Arsenyev Viacheslav A. Kuropatov Vladimir K. Cherkasov Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands Beilstein Journal of Organic Chemistry dioxolene ligand 1,3-dithiole ditopic ligand o-quinone thiete
author_facet	Sergey V. Norkov Anton V. Cherkasov Andrey S. Shavyrin Maxim V. Arsenyev Viacheslav A. Kuropatov Vladimir K. Cherkasov
author_sort	Sergey V. Norkov
title	Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands
title_short	Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands
title_full	Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands
title_fullStr	Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands
title_full_unstemmed	Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands
title_sort	annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. novel ditopic redox-active ligands
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2021-01-01
description	The fused 1,3-dithiole spacer seems to be very suitable for the functionalization of sterically hindered o-quinones with additional groups capable of coordination of metal ions and/or possessing a redox activity. An effective method for the synthesis of sterically hindered o-quinones containing 1,3-diketonate, dinitrile and p-quinone-methide functional groups at the periphery of the ligand has been developed. The novel compounds have rigid and conjugated structures and exhibit properties typical of o-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.
topic	dioxolene ligand 1,3-dithiole ditopic ligand o-quinone thiete
url	https://doi.org/10.3762/bjoc.17.26
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Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands

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