The synthesis and study of a crown ether functionalized with both phosphine and phenol groups

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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.identifier LD2489.Z78 2005 .C72 en_US
dc.identifier.uri http://cardinalscholar.bsu.edu/handle/handle/187955
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.sponsorship Department of Chemistry
dc.format.extent vii, 41 leaves : ill. ; 28 cm. en_US
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
dc.description.degree Thesis (M.S.)
dc.identifier.cardcat-url http://liblink.bsu.edu/catkey/1327790 en_US


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  • Master's Theses [5293]
    Master's theses submitted to the Graduate School by Ball State University master's degree candidates in partial fulfillment of degree requirements.

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