Fluorous chemistry: Difference between revisions
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== References == |
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Revision as of 21:33, 27 January 2009
"Fluorous" is an adjective used to describe methods or materials in chemistry involving use of perfluorinated hydrocarbons such as the common industrial surfactant Perfluorooctanoic acid (PFOA). Due to the extreme electronegativity of fluorine, perfluorinated hydrocarbons have unique physical properties which are useful in organic synthesis and separation methods such as solid phase extraction.[1] In practice, a perfluorinated alkane is often incorporated into an otherwise conventional organic reagent as an affinity tag to facilitate recovery of a catalyst, reaction product, or reaction byproduct. The rationale for using fluorous tags in synthesis or separation is the notion of the fluorous phase, a partitioning modality distinct from polar/non-polar or hydrophilic/hydrophobic.[2] Although many fluorochemicals are known to have toxic effects, the high affinity of fluorous tags for fluorous phases or fluorous-derivatized solid phases allows for near complete recovery of the tagged reagent (i.e., near complete reduction in a chemical waste stream), making the use of fluorous chemistry techniques a popular topic in green chemistry.[3]
References
- ^ Zhang, W.; Curran, D. P. (2006). "Synthetic Applications of Fluorous Solid-Phase Extraction (F-SPE)". Tetrahedron. 62: 11837–11865.
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: CS1 maint: multiple names: authors list (link) - ^ Yu, M. S.; Curran, D. P.; Nagashima, T. (2005). "Increasing Fluorous Partition Coefficients by Solvent Tuning". Org. Lett. 7: 3677–3680.
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: CS1 maint: multiple names: authors list (link) - ^ E.G. Hopea, A.P. Abbotta, D.L. Daviesa, G.A. Solana and A.M. Stuarta “Green Organometallic Chemistry” in Comprehensive Organometallic Chemistry III, 2007, Volume 12, Pages 837-864. doi:10.1016/B0-08-045047-4/00182-5