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The direct metalation of phthalazinium halides with [Rh( t BuO)(COD)] 2 or [Ir( t BuO)(COD)] 2 led to the isolation of stable [MCl(phthalazin-2-ylidene)X(COD)] (M = Rh, Ir) as a new family of cyclic amino aryl carbene transition metal complexes. The X-ray diffraction analysis of several representatives systematically revealed a relatively short C(aryl)−C(carbene) bond distance of 1.44−1.46 Å, shorter than the typical C(sp 2 )−C(sp 2 ) single bond, indicating some electron density delocalization from the π system of the aryl ring over the vacant carbene orbital.
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Magriz et al. (2010) studied this question.
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