Nugent–RajanBabu reagent
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| Names | |
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| Other names
titanocene monochloride
Nugent–RajanBabu reagent |
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| Identifiers | |
| Properties | |
| C20H20Cl2Ti2 | |
| Molar mass | 427.01 g·mol−1 |
| Appearance | green solid |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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 nautrally-occurring alkaloid leurosine.
It was first reported in 1955 by Geoffrey Wilkinson It is commonly prepared by reducing titanocene dichloride with zinc,manganese, or magnesium. For use in organic synthesis, the reagent is often prepared and used directly in situ.
The molecule adopts a dimeric structure with bridging chlorides, though in an appropriate solvent such as THF, exists in a chemical equilibrium with monomeric structures:
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