The phenyl ring in the crown ether, 13-phenyl-1,4,7,10-tetraoxa-13-azacyclopentadecane (I), was used a site for functionalizing the compound. Electrophilic bromination of the ring with tribromide ion gave a 95% yield of the product substituted in the para position. This product underwent lithium-bromine exchange when reacted with n-butyllithium. The resulting anion was used to prepare PhZPX and PhPX2 derivatives, X p-C6H4NCH2(CH2OCH2)4&12 The oxide of PhZPX was completely characterized by an x-ray diffraction study which showed, in general, that the phosphorus was tetrahedral, the nitrogen planar, and the crown ether ring organized with the oxygen atoms endodentate. Several attemps were made to nitrate or nitrosate the phenyl ring in the parent crown ether. Spectroscopic evidence obtained from the products indicate that the reaction led to mixtures of mono and disubstituted products. / Department of Chemistry
| Identifer | oai:union.ndltd.org:BSU/oai:cardinalscholar.bsu.edu:handle/184375 |
| Date | January 1992 |
| Creators | Sheu, Biing-Jahn |
| Contributors | Ball State University. Dept. of Chemistry., Storhoff, Bruce N. |
| Source Sets | Ball State University |
| Detected Language | English |
| Format | xi, 68 leaves : ill. ; 28 cm. |
| Source | Virtual Press |
Page generated in 0.0023 seconds