Tebbe's reagent

Tebbe's reagent
Structure of Tebbe's reagent
Ball-and-stick model of Tebbe's reagent
Names
IUPAC name
μ-Chloro[di(cyclopenta-2,4-dien-1-yl)]dimethyl(μ-methylene)titaniumaluminum
Other names
Tebbe reagent
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.162 Edit this at Wikidata
UNII
  • 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
  • C[Al-]1(C[Ti+2][Cl+]1)C.[cH-]1cccc1.[cH-]1cccc1
Properties
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).
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Tebbe's reagent is the organometallic compound with the formula (C5H5)2TiCH2ClAl(CH3)2. It is used in the methylidenation of carbonyl compounds, that is it converts organic compounds containing the R2C=O group into the related R2C=CH2 derivative.[1] 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.[2] The Tebbe reagent was the first reported compound where a methylene bridge connects a transition metal (Ti) and a main group metal (Al).[3]

  1. ^ F. N. Tebbe, G. W. Parshall and G. S. Reddy (1978). "Olefin homologation with titanium methylene compounds". J. Am. Chem. Soc. 100 (11): 3611–3613. doi:10.1021/ja00479a061.
  2. ^ Thompson, Rick; Nakamaru-Ogiso, Eiko; Chen, Chun-Hsing; Pink, Maren; Mindiola, Daniel J. (2014). "Structural Elucidation of the Illustrious Tebbe Reagent". Organometallics. 33 (1): 429–432. doi:10.1021/om401108b.
  3. ^ Herrmann, W.A., "The Methylene Bridge" Advances in Organometallic Chemistry 1982, 20, 195–197.