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The class of abnormal carbenes, i.e. carbenes for which no neutral canonical resonance form can be drawn, is not restricted to C4-bound imidazolylidenes and includes, for example, also 4-pyrazolylidenes, pioneered by Huynh, and 3-pyridylidenes. For leading references, see:
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33644915013
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Notably, C-H bond oxidative addition at the C4 position requires more forcing conditions when compared with C2-H oxidative addition, indicating that the C2-H is more activated than the C4-H bond. For details, see ref. 18
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0003898591
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P. Braunstein. L. A. Oro and. P. R. Raithby. Wiley-VCH. Weinheim. p. 417. The Pd⋯Pd distance in complex. 35 is 2.9441(6) Å and hence shorter than the sum of the van der Waals radii (3.30 Å). In a related dimeric complex featuring C2-bound dicarbene ligands, the Pd⋯Pd distance is 3.168 Å and hence substantially longer than in. 35, see:
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for an overview, see: J. Forniés and A. Martin, in Metal Clusters in Chemistry, ed., P. Braunstein,,, L. A. Oro, and, P. R. Raithby,, Wiley-VCH, Weinheim, 1999, vol. 1, p. 417
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