Radical cation and dication of a 4H-dithieno[2,3-b:3′,2′-e][1,4]-thiazine‡
Literature Information
Publication Date
2017-04-04
DOI
10.1039/C7QO00188F
Impact Factor
5.281
Authors
Arno Schneeweis, Andreas Neidlinger, Guido J. Reiss, Walter Frank, Katja Heinze, Thomas J. J. Müller
View Original
Abstract
A p-tert-butylphenyl substituted 4H-dithieno[2,3-b:3′,2′-e][1,4]thiazine was synthesized by twofold Buchwald–Hartwig coupling. The electronic properties (UV/Vis, cyclic voltammetry and spectroelectrochemistry) and the DFT- and TD DFT-calculated electronic structure reveal that the parent system and the radical cation and dication oxidation products are highly polarizable π-systems with strong charge transfer contributions. The radical cation and the dication were prepared by oxidation with antimony(V) pentachloride, giving stable deeply colored salts. EPR spectroscopy of the radical cation furnishes hyperfine coupling constants with the nitrogen nucleus and the α-thienyl protons. The dication is EPR silent and was structurally characterized by recording an NMR spectrum.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![(4aR,5S,6R,8aS)-5-[2-(3-Furyl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid structure](https://static.chemtradehub.com/structs/184/18411-75-1-d4cd.webp "(4aR,5S,6R,8aS)-5-[2-(3-Furyl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid structure")
(4aR,5S,6R,8aS)-5-[2-(3-Furyl)ethyl]-8a-(hydroxymethyl)-5,6-dimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid
CAS Number:
18411-75-1
Molecular Formula:
C20H28O4
![2,4-Dichloro-6-isopropyl-5H-pyrrolo[3,4-d]pyrimidin-7(6H)-one structure](https://static.chemtradehub.com/structs/107/1079649-94-7-ad4a.webp "2,4-Dichloro-6-isopropyl-5H-pyrrolo[3,4-d]pyrimidin-7(6H)-one structure")
2,4-Dichloro-6-isopropyl-5H-pyrrolo[3,4-d]pyrimidin-7(6H)-one
CAS Number:
1079649-94-7
Molecular Formula:
C9H9Cl2N3O
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