Tetrakis ethylene dication

Tetrakis(dimethylamino)ethylene dication 224 Acetyl dication 224... 

A variety of dications have recently been prepared and characterized by X-ray diffraction. The tetrakis(dimethylamino)ethylene dication 402 has been generated by... 

Another ethylene dication with significant nitrogen stabilization is the tetrakis(dimethylamino)ethylene dication (88). By reaction of the sub-stituted-ethylene with CI2 or Br2 (eq 23),... 

Kolomeitsev and Roschenthaler [40] produced tetrakis(dimethylamino)ethylene dication stabilized perfluoroaUcyl tliiolates via reduction of bis(perfluoroalkyl)disulfides... 

Scheme 11 Tetrakis(dimethylamino)ethylene dication trifluoromethyl thiolate as a stable reagent for substitution of aromatic halides...

Slow crystallization of salt from the reaction solution layered with diethyl ether leads to the formation of a mixture of tetrakis(anisyl)ethylene cation-radical and dicationic salts along with tetrakis( anisyl)ethylene. All the compounds precipitate from the solution containing the cation-radical salt only. The formation of dication is a result of disproportionation. 

Tetrakis(dimethylamino)ethylene (TKDE) is a strong electron donor which oxidizes to radical-cation and dication states similar to the well-known Wurster s radicals. Cyclic... 

The anodic behavior of A -substituted alkenes can be described as the oxidation of an electron-rich double bond. Tetraamino-substituted alkenes are extremely easily oxidized. Tetrakis(dimethylamino)ethylene exhibits two reversible one-electron processes at —0.75 and —0.61 V vs. SCE at a dropping mercury electrode in acetonitrile [140]. The anodic behavior of A, A -dimethylaminoalkenes has been studied intensively by cyclic voltammetry and electron spin resonance (ESR) spectroscopy [141]. The anodically E° = 0.48 V vs. SCE) generated cation radical of l,l-bis(iV,iV-dimethylamino)ethylene is shown to undergo C-C coupling, forming l,l,4,4-tetrakis(A, iV-dimethylamino)butadiene, which subsequently is further oxidized to its dication at —0.8 V [141,142]. With vicinal diamino ethylenes, usually two reversible one-electron oxidations are observed [143], while gem-inal diamino ethylenes exhibit an irreversible behavior [141]. Aryl-substituted vicinal diamino ethylenes (endiamines) can undergo a double cyclization to give an indolo-oxazoline when oxidized at 0.4 V vs. SCE in acetonitrile in the presence of 2,6-lutidine [144] ... 

Pruett was the first to observe that the action of a halogen on a peraminoethylene (1) yielded a salt-like dihalide. Carrying out similar experiments with tetrakis(aralkylamino) ethylene (5), Kawano characterized the dication and identified the oxidation-state intermediate between ethylene and dication. When such oxidizing agents as iodine or silver salts were added to acetonitrile solutions of 5 the intense violet color characteristic of radical-cation 90 (A 517 m x. 

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