Tebbe's reagent

<p>Tebbe's reagent is the <a href="/facts/Organometallic_compound/bhqFz2P0">organometallic compound</a> with the formula (C5H5)2TiCH2ClAl(CH3)2. It is used in the <a href="/facts/Methylidene_group/bEIzaSd0">methylidenation</a> of <a href="/facts/Carbonyl/KJ71bo3X">carbonyl</a> compounds, that is it converts organic compounds containing the R2C=O group into the related R2C=CH2 derivative. It is a red solid that is <a href="/facts/Pyrophoric/1b8Sl2AJ">pyrophoric</a> in the air, and thus is typically handled with <a href="/facts/Air-free_technique/pEW9wY6e">air-free techniques</a>. It was originally synthesized by <a href="/facts/Fred_Tebbe/trLPx8ed">Fred Tebbe</a> at <a href="/facts/DuPont_Central_Research/Ivj9n2Kk">DuPont Central Research</a>.
</p><p>Tebbe's reagent contains two <a href="/facts/Tetrahedral_molecular_geometry/583AL1sP">tetrahedral</a> metal centers linked by a pair of <a href="/facts/Bridging_ligand/E4ytba8I">bridging ligands</a>. The titanium has two <a href="/facts/Cyclopentadienyl_complex/rezSmzLI">cyclopentadienyl</a> ([C5H5]−, or  Cp) rings and aluminium has two methyl groups. The titanium and aluminium atoms are linked together by both a <a href="/facts/Methylene_bridge/t3lvUJuT">methylene bridge</a> (-CH2-) and a chloride atom in a nearly <a href="/facts/Square_planar_molecular_geometry/2mLqCvd0">square-planar</a> (Ti–CH2–Al–Cl) geometry.  The Tebbe reagent was the first reported compound where a methylene bridge connects a transition metal (Ti) and a main group metal (Al).
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Tebbe's reagent open-in-new

Tebbe's reagent