The synthesis and study of an amine functionalized crown ether

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dc.contributor.advisor Storhoff, Bruce N. en_US Yonekawa, Sayuri en_US 2011-06-03T19:40:09Z 2011-06-03T19:40:09Z 2004 en_US 2004
dc.identifier LD2489.Z78 2004 .Y66 en_US
dc.description.abstract This study has resulted in a route to the first known NHZ functionalized xylenebased crown ether, 5-amino-2-methoxy-1,3-xylyl-18-crown-5. The route involves preparing 5-azido-2-methoxy-1,3-xylyl-18-crown-5 from 5-bromo-2-methoxy-1,3-xylyl18-crown-5 by reacting it in turn with n-BuLi and tosyl azide. 5-Amino-2-methoxy-1,3xylyl-l8-crown-5 was obtained by reducing 5-azido-2-methoxy-1,3-xylyl-l8-crown-5 with aqueous sodium borohydride in the presence of a phase transfer agent. The 'H NMR spectrum of the amino derivative showed NMR signals at 6 3.4-3.7 (crown CHZ), S 4.0 (benzylic), S 4.47 (methoxy), and 6 6.58 (aromatic) ppm. The integrated areas were consistent with the formula, and they also suggested the NH2 protons were in the crown CH2 area. The IR (KBr pellet) spectrum showed bands at 3408 cm' and 3364 cm' corresponding to the N-H asymmetric and symmetric stretches, respectively. This study has also provided a new procedure for the preparation of 4-bromo-2,6-bis(bromomethyl) anisole, which was the intermediate for 5-bromo-2-methoxy-1,3-xylyl-18-crown-5. It involved reacting 4-bromophenol in turn with 30 % formaldehyde, dimethylsulfate, and HBr in acetic acid.
dc.description.sponsorship Department of Chemistry
dc.format.extent vii, 50 leaves : ill. ; 28 cm. en_US
dc.source Virtual Press en_US
dc.subject.lcsh Crown ethers. en_US
dc.subject.lcsh Nitriles. en_US
dc.title The synthesis and study of an amine functionalized crown ether en_US Thesis (M.S.)
dc.identifier.cardcat-url en_US

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  • Master's Theses [5510]
    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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