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Oxidation and reduction of 2,2-bis(diethylamino)-2-ethylium-1-dithioate

✍ Scribed by Takashi Otani; Yoshiaki Sugihara; Akihiko Ishii; Juzo Nakayama


Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
175 KB
Volume
9
Category
Article
ISSN
1042-7163

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✦ Synopsis


Oxidation of the titled inner salt 1 with a typical one-electron oxidizing reagent, NOPF 6 , produced the radical cation 5a, whose dimerization, followed by loss of a sulfur atom, led to the formation of the bis-carbenium salt 4a in 95% yield. Moreover, reduction of 1 with a typical one-electron reducing reagent, lithium naphthalenide, produced the ethene-1,1-dithiolate 16, which was converted to the ethene 17 in 73% yield by treatment with methyl iodide. Also reported are synthetic applications of the oxidation of 1 with bromine and the reduction with LiEt 3 BH.


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3, were synthesized by cyclization of 4-propylthio-1,2-phenylenediamine ( 3) with the corresponding dichlorophosphoryl carbamates/thiocarbamates (2a-J) that were obtained by the addition of alcohols/thiols to isocyanatophosphoryl dichloride (1). The structures of the title compounds were confirme