Tebbe reagent

Tebbe's reagent

Names
IUPAC name μ-Chloro[di(cyclopenta-2,4-dien-1-yl)]dimethyl(μ-methylene)titaniumaluminum
Other names Tebbe reagent
Identifiers
CAS Number	67719-69-1 Y
3D model (JSmol)	Interactive image
ChemSpider	34981139 N
ECHA InfoCard	100.157.162
PubChem CID	53384502
InChI InChI=1S/2C5H5.2CH3.CH2.Al.Cl.Ti/c2*1-2-4-5-3-1;;;;;;/h2*1-5H;2*1H3;1H2;;;/q2*-1;;;;-1;+1;+2 N Key: FHPQZKBPAZOMGO-UHFFFAOYSA-N N InChI=1/2C5H5.2CH3.CH2.Al.Cl.Ti/c2*1-2-4-5-3-1;;;;;;/h2*1-5H;2*1H3;1H2;;;/q2*-1;;;;-1;+1;+2/r2C5H5.C3H8AlClTi/c2*1-2-4-5-3-1;1-4(2)3-6-5-4/h2*1-5H;3H2,1-2H3/q2*-1;+2 Key: FHPQZKBPAZOMGO-SBUAZLESAR
SMILES C[Al-]1(C[Ti+2][Cl+]1)C.[cH-]1cccc1.[cH-]1cccc1
Properties
Chemical formula	C13H18AlClTi
Molar mass	284.60 g/mol
Solubility in other solvents	toluene, benzene, dichloromethane, THF (low temperatures only)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

The Tebbe reagent is the organometallic compound with the formula (C₅H₅)₂TiCH₂ClAl(CH₃)₂. It is 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 metal centers linked by a pair of bridging ligands. The titanium has two cyclopentadienyl ([C
₅H
₅]⁻
, or Cp) rings and aluminium has two methyl groups. The titanium and aluminium atoms are linked together by both a methylene bridge (-CH₂-) and a chloride atom in a nearly square-planar (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).

The Tebbe reagent is synthesized from titanocene dichloride and trimethylaluminium in toluene solution.