The synthesis and study of a crown ether functionalized with both phosphine and phenol groups
| dc.contributor.advisor | Storhoff, Bruce N. | en_US |
| dc.contributor.author | Crabill, Todd W. | en_US |
| dc.date.accessioned | 2011-06-03T19:40:34Z | |
| dc.date.available | 2011-06-03T19:40:34Z | |
| dc.date.created | 2005 | en_US |
| dc.date.issued | 2005 | |
| dc.description.abstract | This study has resulted in a crown ether functionalized with both phosphine and phenol groups, 5-diphenylphosphino-1,3-xylyl-18-crown-5. The target molecule was obtained from a six step synthesis. 4-Bromophenol was treated in sequence with formaldehyde, dimethylsulfate, and phosphorus tribromide producing 4-bromo-2,6-bis(bromomethyl)anisole. The main intermediate, 5-diphenylphosphino-1,3-xylyl-18-crown-5, was obtained by treating 4-bromo-2,6-bis(bromomethyl)anisole in sequence with tetraethylene glycol, lithium iodide, and methyldiphenyl phosphonite. The lithium iodide cleaved the anisole-to-methyl group bond, and the methyldiphenyl phosphonite provided the phosphine group for the crown ether following a lithium bromine exchange reaction. The 31P NMR of the phosphine crown ether showed a single signal at 6 -5.9, showing consistency of a single product. The IH NMR of the phosphine crown ether in deuterated chloroform showed signals at 6 3.55-3.7 (crown CH2), 6 4.6 (benzylic CH2), 6 7.1 (d, J = 7.o Hz, crown aromatic CH2), and 6 7.2-7.4 (noncrown aromatic CH2). | |
| dc.description.degree | Thesis (M.S.) | |
| dc.description.sponsorship | Department of Chemistry | |
| dc.format.extent | vii, 41 leaves : ill. ; 28 cm. | en_US |
| dc.identifier | LD2489.Z78 2005 .C72 | en_US |
| dc.identifier.cardcat-url | http://liblink.bsu.edu/catkey/1327790 | en_US |
| dc.identifier.uri | http://cardinalscholar.bsu.edu/handle/20.500.14291/187955 | |
| dc.source | Virtual Press | en_US |
| dc.subject.lcsh | Crown ethers -- Synthesis. | en_US |
| dc.subject.lcsh | Phosphine -- Synthesis. | en_US |
| dc.subject.lcsh | Phenols -- Synthesis. | en_US |
| dc.title | The synthesis and study of a crown ether functionalized with both phosphine and phenol groups | en_US |
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