The reaction of 1,1-bis(dialkylamino)ethenes ( ) with an equimolar amount of disulfur dichloride in the presence of triethylamine affords the stable inner salts 2,2-bis(dialkylamino)-2-ethylium-1-dithioates (1) in good yields.
Oxidation and reduction of 2,2-bis(diethylamino)-2-ethylium-1-dithioate
β 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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β¦ 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.
π SIMILAR VOLUMES
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