Selective synthesis and reactivity of eta(5)-arylcyclohexadienyliron complexes

Owen, David A., Malkov, Andrei V., Palotai, Ian M., Roe, Caroline, Sandoe, Elizabeth J. and Stephenson, G. Richard ORCID: (2007) Selective synthesis and reactivity of eta(5)-arylcyclohexadienyliron complexes. Chemistry - A European Journal, 13 (15). pp. 4293-4311. ISSN 0947-6539

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A series of aryl-substituted cyclohexadienyliron complexes have been prepared by a general procedure that determines regioselectivity by correctly positioning leaving groups in the precursor complexes. The aryl groups at 1-C or 2-C have been shown to be omega directing by the study of reactions with a representative range of nucleophiles, and these regioselectivity properties have been related to the spectroscopic properties of the cationic cyclohexadienyliron complexes. A high level of electron-donating substituents on the arene, or switching between the [Fe(CO)(3)] and [Fe(CO)(2)PPh3] series, reduces the minor ipso pathway, improving regiocontrol. Placing opposed directing groups in the arylcyclohexadienyliron complexes reverts reactivity to the ipso pathway with stabilised enolate nucleophiles, and when the additional directing group reinforces the effect of the aryl group, the ipso pathway is stopped.

Item Type: Article
Additional Information: Owen, David A. Malkov, Andrei V. Palotai, Ian M. Roe, Caroline Sandoe, Elizabeth J. Stephenson, G. Richard
Faculty \ School: Faculty of Science > School of Chemistry
UEA Research Groups: Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User: Rachel Smith
Date Deposited: 08 Jun 2011 10:49
Last Modified: 24 Oct 2022 01:28
DOI: 10.1002/chem.200601513

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