DCPTC reagent
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Novasep Synthesis Proprietary Products: DCPTC Reagent
Reagent / Catalyst
DCPTC / Dicyclopentadienyltitanium dichloride
| Formula | C10H10Cl2Ti |
| Molecular Mass | 249.0 g/mol |
| CAS-No. | [1271-19-8] |
| EINECS | 215-035-9 |
| Scale of Development | Commercial |
Specification
| Appearance | red to red brown solid |
| Identity | conforms (IR) |
| Iron | < 20 ppm (AAS) |
| Melting Point | >= 280°C (DSC) |
| Assay | 98 to 102 % (Argentometric) |
Transport Information
| Transport classification | Non dangerous goods according to transport regulations |
| Packaging | Fibre drums, PE-Inliner, 50 kg |
| Sample Size | 50 g or 1 kg |
| Availability | Samples available |
Quality / Regulatory
Non-GMP product, the synthesis of this product can be performed under c-GMP upon request / agreement. Please feel free to ask for more information.
Contact
Applications
- Catalyst in the syntheses of anti-emetic, anti-depressant and analgesic API's
- Metallocene catalyst for polymerizations, Novasep is ready to develop other Metallocene catalysts
- Synthone for methylene compounds (olefinisation) and vinylethers
- Educt for Petasis Reagent and Tebbe's Reagent
- In the electronic industry
- Novasep has a long track record in the production of commercial quantities.
DCPTC can be used as cocatalyst in polymerization reactions e.g. for polypropylene.
The titanocene family has been investigated as potential anti-cancer drugs
(currently only in clinical trials).
Application in organic synthesis:
- DCPTC is a generally useful reagent that effectively behaves as a source of Cp2Ti2+. Thus, a large range of nucleophiles will substitute chloride.
- The Petasis reagent, Cp2Ti(CH3)2, is prepared from the reaction of CH3MgCl or MeLi with Cp2TiCl2.
This reagent is useful for the conversion of esters into vinyl ethers. - The Tebbe's reagent Cp2TiCl(CH2)Al(CH3)2 is formed by the reaction of 2 equivalents Al(CH3)3 on Cp2TiCl2. This reagent is useful for the methylenation of carbonyl compounds.
- Cp2TiCl2 can be used in a novel method of a Reformatsky-like reaction.
- Cp2TiCl2 undergoes anion exchange reactions.
- Cp2TiCl2 can be stripped of one Cp ligand to give tetrahedral CpTiCl3 by reaction with TiCl4 or by reaction with SOCl2.
Examples
Petasis reagent: Cp2Ti(CH3)2
The synthesis of pyruvate-based enol ethers and enamines via the Petasis olefination has been demonstrated by Timothy Gallagher and co-workers from the University of Bristol. The olefination of unsymmetrical oxalates is highly regioselective by employing the Petasis reagent and is dramatically improved when microwave heating is applied. Shorter reaction times and higher yields are achieved by irradiating in toluene/THF for 0.5-3 hours at 120-150 °C.
Cook, M. J.; Fleming, D. W.; Gallagher, T.; Tetrahedron Letters, Volume 46,
Issue 2, 10 January 2005, Pages 297-300
Tebbe reagent: Cp2TiCH2ClAl(CH3)2
Tebbe reagent is used in the methylenation of carbonyl compounds
Cp2TiCl2 + 2 Al(CH3)3 -------> CH4 + Cp2TiCH2AlCl(CH3)2 + Al(CH3)2Cl
Tebbe reagent is more efficient for sterically encumbered carbonyls, less basic than the Wittig reagent and does not give the β-elimination products.
Methylenation reactions also occur for aldehydes as well as esters, lactones and amides. The Tebbe reagent converts esters and lactones into enol ethers and amides into enamines. In compounds containing both ketone and ester groups, the ketone selectively reacts in the presence of one equivalent of the Tebbe reagent.
The Tebbe reagent methylenates carbonyls without racemizing a chiral α-carbon. For this reason, the Tebbe reagent has found applications in reactions of sugars where maintenance of stereochemistry can be critical.
Pine, S. H. Org. React. 1993, 43, 1. (Review)
Beadham, I.; Micklefield, J. Curr. Org. Syn. 2005, 2, 231-250. (Review)
Marra, A.; Esnault, J.; Veyrieres, A.; Sinay, P. "Isopropenyl glycosides and congeners as novel classes of glycosyl donors: theme and variations" J. Am. Chem. Soc. 1992, 114, 6354-6360.
Titanocene(III)-Promoted Reformatsky Additions:
A novel method for Reformatsky-like reactions employs titanocene(III) chloride as a mild and homogeneous single-electron reductant. The reactions are simple, rapid and tolerate a wide range of functionalities. The addition is anti-selective.
| Product | Yield* | Product | Yield* |
 |
90 |  |
78 |
 |
94 |  |
92 |
(*) %, isol.
Parrish, J. D.; Shelton, D. R.; Little, R. D.; Org. Lett., 2003, 5, 3615-3617.
Electronic Materials
No example available
Contact
reagents@novasep.comMitsunobu reagents
MAME reagent
DCPTC reagent/catalyst
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