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THE SYNTHESIS, REDUCTION, AND CHLORINATION OF 5-ALKOXY-2,3-DIPHENYLTEREPHTHALATES

Sayers, Rachel Marie
http://rave.ohiolink.edu/etdc/view?acc_num=wright1309375974

Abstract Details

2011, Master of Science (MS), Wright State University, Chemistry.
A series of alkoxy, phenylated terephthalates has been synthesized as monomer precursors to the corresponding poly(phenylene vinylene)s (PPV). The hydroxy, phenylated terephthalate was synthesized via: 1) a Diels-Alder cycloaddition between an ethynyl boronic ester and a cyclopentadienone (CPD) with subsequent hydrolysis/oxidation of the boronate ester or 2) a Diels-Alder cycloaddition between vinylene carbonate and CPD followed by thermolysis of the bridged adduct. The hydroxy, phenylated terephthalate was alkylated via a phase-transfer reaction with iodomethane, propargyl bromide, benzyl chloride, allyl bromide, and bromobutane to produce the alkoxy, phenylated terephthalates in yields from 38.6- 91.1%. The alkoxyterephthlates were reduced with lithium aluminum hydride to either the corresponding 5-alkoxy- (methoxy, benzyloxy) or 5-hydroxy-1,4-di(hydroxymethyl)-3,4-diphenylbenzene (allyloxy, propargyloxy) in yields from 40.9-94.0%. The methoxy and benzyloxy-1,4-di(hydroxymethyl)-3,4-diphenylbenzenes were reacted with thionyl chloride to yield the corresponding 1,4-di(chloromethyl)-3,4-diphenylbenzenes. The polymerization of 5-methoxy-1,4-di(chloromethyl)-3,4-diphenylbenzene with t-BuOK yielded the insoluble polymer 5-methoxy-2,3-diphenyl-1,4-poly(phenylene vinylene).
William Feld, PhD (Advisor)
Kenneth Turnbull, PhD (Committee Member)
Eric Fossum, PhD (Committee Member)
119 p.
Chemistry
phenylated terephthalates; poly(phenylene vinylene)s; Diels-Alder; phase-transfer; alkoxyterephthlates

Recommended Citations

Citations

  • Sayers, R. M. (2011). THE SYNTHESIS, REDUCTION, AND CHLORINATION OF 5-ALKOXY-2,3-DIPHENYLTEREPHTHALATES [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1309375974

    APA Style (7th edition)

  • Sayers, Rachel. THE SYNTHESIS, REDUCTION, AND CHLORINATION OF 5-ALKOXY-2,3-DIPHENYLTEREPHTHALATES. 2011. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1309375974.

    MLA Style (8th edition)

  • Sayers, Rachel. "THE SYNTHESIS, REDUCTION, AND CHLORINATION OF 5-ALKOXY-2,3-DIPHENYLTEREPHTHALATES." Master's thesis, Wright State University, 2011. http://rave.ohiolink.edu/etdc/view?acc_num=wright1309375974

    Chicago Manual of Style (17th edition)

wright1309375974
867
© 2011, all rights reserved.
This open access ETD is published by Wright State University and OhioLINK.