A new fluorous/organic amphiphilic ether solvent, F-626: execution of fluorous and high temperature classical reactions with convenient biphase workup to separate product from high boiling solvent

摘要

A new fluorous/organic amphiphilic ether solvent, 1H,1H,2H,2H-perfluorooctyl 1,3-dimethylbutyl ether (F-626), is introduced. The basic properties of F-626, especially the partition coefficients with organic solvents/FC-72 (perfluorohexane), were investigated. F-626 was easy to remove by fluorous biphase treatment. Using F-626 as a solvent, LAH reduction, catalytic hydrogenation, and fluorous reductive radical reactions were successful. Classical high temperature reactions up to 200degreesC, such as the Vilsmeier formylation, the Wolff-Kishner reduction, and the Diels-Alder reaction, were also examined in F-626. The yields of the products in F-626 were almost comparable with those conducted in common organic solvents, which prove that F-626 has the potential to be an easily recyclable high boiling solvent. (C) 2002 Elsevier Science Ltd. All rights reserved. [References: 37]