The synthesis and study of new phosphines functionalized with crown ethers

The goal of this research was to synthesize and study new phosphine crown ethers. The first target molecule was 5-phenylphoshinobis(2-hydroxy,1,3-xylyl-18-crown-5). We tried to synthesize this target molecule in six steps. 5-Bromophenol was reacted with formaldehyde, dimethylsulfate, phosphorus tribromide and tetraethylene glycol in the presence of sodium hydride producing the main intermediate molecule, 5-bromo-2-methoxy-1,3-xylyl-l8-crown-5. This molecule was reacted with n-butyllithium and dimethyl phenylphosphinite at the low temperature . NMR evidence indicated that was not obtained.The second target molecule, the oxide of 5-phenylphosphinobis(2-hydroxy-1,3-xylylcrown-5) was synthesized in nine steps. The main intermediate, 5-bromo-2-methoxy-1,3-xylyl-18-crown-5 was reacted with n-butyllithium and dimethyl phenylphosphinite to form the phosphine. This phosphine was oxidized with hydrogen peroxide. The OCH3 bond of this crown ether was cleaved by using LiI in boiling anhydrous pyridine. NMR data indicated the product was formed.Department of ChemistryThesis (M.S.