5 years ago

A Stable Anionic Dithiolene Radical

A Stable Anionic Dithiolene Radical
Gregory H. Robinson, Henry F. Schaefer, Hunter P. Hickox, Yaoming Xie, Yuzhong Wang, Soshawn A. Blair, Pingrong Wei, Michael K. Johnson
Sulfurization of anionic N-heterocyclic dicarbene, [:C{[N(2,6-Pri2C6H3)]2CHCLi}]n (2), with elemental sulfur (in a 1:2 ratio) in Et2O at low temperature gives 3 by inserting two sulfur atoms into the Li–C (i.e., C2 and C4) bonds in polymeric 2. Further reaction of 3 with 2 equiv of elemental sulfur in THF affords 4 via unexpected C–H bond activation, which represents the first anionic dithiolene radical to be structurally characterized in the solid state. Alternatively, 4 may also be synthesized directly by reaction of 1 with sulfur (in a 1:4 ratio) in THF. Reaction of 4 with GeCl2·dioxane gives an anionic germanium(IV)–bis(dithiolene) complex (5). The nature of the bonding in 4 and 5 was probed by experimental and theoretical methods.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b03794

DOI: 10.1021/jacs.7b03794

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