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doi:10.1016/j.jfluchem.2007.09.007 
Copyright © 2007 Elsevier B.V. All rights reserved.
Preparation of ferrocenes with high fluorous-phase affinities
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W. Gary Hollis Jr.
, a, 
, Matthew G. Poferla, 1, Michael D. Woltera, 1, Paul A. Deckb and Carla Slebodnickb
Received 15 September 2007;
Abstract
The reaction of 1,1′-bis(pentafluorophenyl)ferrocene with fluorous alkoxides having the general formula NaOCH2(CF2)nCF3 (n = 0, 2, 5, 7, and 8) afforded a series of ferrocenes of general formula {η5-4-[CF3(CF2)nCH2O]C6F4C5H4}2Fe (1). The reaction of 1,1′-bis(4-tetrafluoropyridyl)ferrocene with the same fluorous alkoxides afforded a series of ferrocenes of general formula (η5-4-{2,6-[CF3(CF2)nCH2O]2C5F2N}C5H4)2Fe (2). Perfluoro(methylcyclohexane)/toluene partition coefficients increase with the number (2 or 4) and length (n) of the fluorous substituent. Complexes 1a and 2a (both n = 0) were structurally characterized.
Graphical abstract
Ferrocenes bearing either C6F5 or C5F4N substituents undergo ready nucleophilic substitution by fluorous alcohols to yield compounds bearing either 2 or 4 OCH2(CF2)nCF3 “ponytails.” These substituents effect high fluorous-phase affinities as measured by UV–vis spectrophotometry.
Keywords: Fluorous-phase affinity; Ferrocene; Biphase; Nucleophilic substitution; UV–vis
Article Outline
4JHH Corresponding author. Tel.: +1 540 375 2437; fax: +1 540 375 2055.1 Undergraduate research participant.
