Bis(cyclopentadienyl)titanium(III) chloride

Bis(cyclopentadienyl)titanium(III) chloride
Names
Other names
titanocene monochloride
Nugent–RajanBabu reagent
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/2C5H5.ClH.Ti/c2*1-2-4-5-3-1;;/h2*1-5H;1H;/p-1
    Key: GCXNJJRCRJQDSV-UHFFFAOYSA-M
  • monomer: c1[cH-]ccc1.Cl[Ti+2].c1[cH-]ccc1
  • dimer: c1[cH-]ccc1.c1[cH-]ccc1.Cl1[Ti+2]Cl[Ti+2]1.c1[cH-]ccc1.c1[cH-]ccc1
Properties
C20H20Cl2Ti2
Molar mass 427.01 g·mol−1
Appearance green solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bis(cyclopentadienyl)titanium(III) chloride, also known as the Nugent–RajanBabu reagent, is the organotitanium compound which exists as a dimer with the formula [(C5H5)2TiCl]2. It is an air sensitive green solid. The complex finds specialized use in synthetic organic chemistry as a single electron reductant.

In the presence of a suitable solvent that can act as a two-electron donor ("solv"), such as an ether like tetrahydrofuran, the dimer separates and forms a chemical equilibrium between the forms [(C5H5)2TiCl] and [(C5H5)2Ti(solv)Cl]. It is these forms that are responsible for much of the chemical properties of this reagent, which is also the reason that the substance is sometimes written as [(C5H5)2TiCl] or [Cp2TiCl], where Cp represents the cyclopentadienyl anion.

An example of an application of this reagent is in the preparation of vinorelbine, a chemotherapeutic agent which can be prepared in three steps from the naturally-occurring alkaloid leurosine.