A Viable Anionic N-Heterocyclic Dicarbene
Journal of the American Chemical Society2010Vol. 132(41), pp. 14370–14372
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Yuzhong Wang, Yaoming Xie, M.Y. Abraham, Pingrong Wei, Henry F. Schaefer, Paul von Ragué Schleyer, Gregory H. Robinson
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)].
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