The Synthesis of Organometallic YlidesInteraction of Methylenetriphenylphosphorane with Bis(η5-cyclopentadienyl)-zirconium and -hafnium Dichlorides and the Molecular Structure of Bis(η5 -Cyclopentadienyl)chlorozirconylmethylenetriphenylphosphorane

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Abstract
The interaction of (η5-C5H5)2MCl2 (M = Zr, Hf) with excess C̅H2-P⁺Ph3 in THF gives (η5-C5H5)2MCl(C̅H-P⁺Ph3) as yellow orange needles. Nuclear magnetic resonance spectra show hindered rotation about the P⁺-C̅ bond with ⊿G≠= 8.6 kcal/mole for M = Zr and 8.3 kcal/mole for M - Hf, respectively. The X-ray molecular structure of the zirconium complex shows a relatively short Zr-C bond length of 2.152 Å and a long P⁺-C̅ bond length of 1.716 Å.