Tebbe's Reagent

Tebbe's Reagent

The Tebbe reagent is the organometallic compound with the formula (C5H5)2TiCH2ClAl(CH3)2. It used in the methylenation of carbonyl 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 pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research.

Tebbe's reagent contains two tetrahedral centers linked by a pair of bridging ligands. Titanium features two cyclopentadienyl (−, or Cp) rings, and aluminium features two methyl ligands. The titanium and aluminium atoms are joined by both a methylene bridge (-CH2-) and by chloride ligands. This compound exhibits a nearly square (Ti-CH2-Al-Cl) bridge. 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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