The synthesis and study of phosphine functionalized crown ethers with fluorine in positions to assist with ion binding : an honors thesis (HONRS 499)

Abstract

Phosphine-crown ethers based on 1,3-xylyl-l8-crown-5 units with fluorine atoms in the 2-positions and P(III) donors in the 5-positions have been synthesized and characterized. The starting materials for the crown ether portions of the molecules were 4-bromo-2,6-dimethylaniline, NaBF4, NBS and tetraethylene glycol. The P(III) moieties have been introduced by generating the carbanions at the 5-positions by way of Br-Li exchange reactions. The procedures used during the synthesis along with the spectroscopic characteristics of the intermediates and final products will be discussed.