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Cp_2TiCH_2 complexes in synthetic applications

Brown-Wensley, K. A. and Buchwald, S. L. and Cannizzo, L. and Clawson, L. and Ho, S. and Meinhardt, D. and Stille, J. R. and Straus, D. and Grubbs, R. H. (1983) Cp_2TiCH_2 complexes in synthetic applications. Pure and Applied Chemistry, 55 (11). pp. 1733-1744. ISSN 0033-4545. doi:10.1351/pac198355111733.

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The reactive 16e- species Cp_2Ti=CH_2 can be generated in situ from either its aluminum alkyl adducts or olefin adducts (metallacyclobutanes). This complex reacts with a wide variety of unsaturated functionalities including c=O, c=C,-c≡c- and –C≡N. In most instances the c:O groups are methylenated. Key to the utility of these complexes is their lack of basic properties in contrast with phosphorous ylides; all of the normal "Wittig" side reactions are eliminated using these reagents. Acid chlorides and anhydrides are converted into enolate complexes, which can be used in aldol type chemistry. The combination of the reactivity toward C=O and C=C results in an efficient method for the conversion of unhindered carbonyl centers into quarternary carbon centers.

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Grubbs, R. H.0000-0002-0057-7817
Alternate Title:Cp2TiCH2 complexes in synthetic applications
Additional Information:© 1983 IUPAC. The authors gratefully acknowledge the financial support of the National Science Foundation and the National Institutes of Health.
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Caltech Laboratories of Chemistry6891
Issue or Number:11
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88652
Deposited By: Tony Diaz
Deposited On:08 Aug 2018 17:23
Last Modified:16 Nov 2021 00:28

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