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A viable anionic N-heterocyclic dicarbene

Wang, Y.; Xie, Y.; Abraham, M. Y.; Wei, P.; Schaefer, H. F., 3rd; Schleyer, P. R.; Robinson, G. H. A viable anionic N-heterocyclic dicarbene. Journal of the American Chemical Society 2010, 132, 14370-2.

Abstract

The first anionic N-heterocyclic dicarbene, polymeric [:C{[N(2,6-Pr(i)(2)C(6)H(3))](2)CHCLi(THF)}](n) 1, containing both normal (C2) and abnormal carbene (C4) centers in the same five-membered imidazole ring (III), has been prepared by lithiation of the imidazole monocarbene, :C{N(2,6-Pr(i)(2)C(6)H(3))CH}(2). The dicarbene nature of 1 was unambiguously demonstrated by the formation of the group 13 Lewis acid adducts (THF)(2)Li:C{[N(2,6-Pr(i)(2)C(6)H(3))](2)CHC(LA)}, where LA = AlMe(3) [2.(THF)(2)] and BEt(3) [3.(THF)(2)].