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Perfluoroalkylated 4,13-diaza-18-crown-6 ethers: Synthesis, phase transfer catalysis and recycling studies.

By A. M. Stuart and J. A. Vidal


A series of N,N‘-dialkyl-4,13-diaza-18-crown-6 lariat ethers possessing two C8H17 (2), (CH2)3C8F17 (3), (CH2)3C10F21 (4), and (CH2)2C8F17 (5) side arms were synthesized in good yields by N-alkylation of 4,13-diaza-18-crown-6. Potassium picrate could be extracted from an aqueous solution into an organic phase by all of the perfluoroalkylated macrocycles demonstrating their potential to be used as phase-transfer catalysts, and preliminary studies on a classical nucleophilic substitution established that they each gave higher catalytic activities under solid−liquid than under liquid−liquid phase-transfer conditions. The light fluorous macrocycles gave similar, if not better, catalytic activity compared to the parent, non-fluorinated phase-transfer catalyst 2 under solid−liquid conditions in conventional organic solvents in both an aliphatic and an aromatic nucleophilic substitution. N,N‘-Bis(1H,1H,2H,2H,3H,3H-perfluoroundecyl)-4,13-diaza-18-crown-6 (3) was recycled six times in the iodide displacement reaction of 1-bromooctane and four times in the fluoride displacement reaction of 2,4-dinitrochlorobenzene using fluorous solid-phase extraction without any loss in activity

Year: 2007
DOI identifier: 10.1021/jo062606x
OAI identifier: oai:lra.le.ac.uk:2381/634
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