(Tebbe Methylenation, Tebbe Reaction)
Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Tebbe Olefination. Comprehensive Organic Name Reactions and Reagents. 617:2753–2757.
- Published Online: 15 SEP 2010
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The transformation of a carbonyl group into a terminal vinyl group by means of low-valent titanium alkylidene complexes, especially a methylene complex prepared from titanocene dichloride and trimethylaluminum—that is, [Cp2Ti(μ-CH2)(μ-Cl)Al(CH3)2] generally referred to as the Tebbe olefination. The heterobimetallic alkylidene-bridged complex is known as the Tebbe reagent. It has been reported that the Tebbe reagent also catalyzes alkene metathesis reaction, a manner analogous to the Grubb catalysts, in the presence of a high steric hindrance and electron-rich olefin (e.g., norbornene). The study finds that the Tebbe reagent gives the best results within the first five days after preparation. This reaction has been applied in carbohydrate transformations in conjunction with the Ferrier rearrangement.
- titanocene dichloride;