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MS (Master of Science)
Date of Award
Committee Chair or Co-Chairs
Hamid S. Kasmai
Jeffrey G. Wardeska, Tammy A. Davidson
Iminium salt dimethyliminium hexafluorophosphate (5), a precursor of the target compound BPDO-TTF, was synthesized in five steps with significant modifications in the previously worked out scheme. 2,3-Dihydrobenzo-1, 4-dioxin(1) was synthesized from catechol in a strongly alkaline medium. Compound (1) was dichlorinated with SO2Cl2 to give 2,3-dichloro-2,3-dihydrobenzo-1,4-dioxin (2). Subsequent reaction of compound (2) with sodium dimethyldithiocarbamate followed by dehydrochlorination in triethyl amine gave 1,4-Benzodioxin-2-N,N-dimethyldithiocarbamate (3). Bromination of compound (3) followed by treatment with hexafluorophosphoric acid yielded bromo-dimethyliminium hexafluorophosphate (4). Dehydrobromination of compound (4) by solid phase thermolysis reaction resulted in dimethyliminium hexafluorophosphate (5). In an effort to prepare BPDO-TTF from a coupling reaction of dithioselenone (7), the dimethyl iminium salt (5) was reacted with NaHSe; however, no pure dithioselenone was isolable from the reaction mixture. A photochemical coupling reaction was also attempted using dimethyl iminium salt (5) and trimethyl phosphite but the desired product did not form in a detectable amount.
Thesis - Campus Only
Biswas, Debanjan, "A Modified Procedure for the Synthesis of Bis(phenylenedioxy)tetrathiafulvalene (BPDO-TTF): an Electron Donor for Charge Transfer Organic Complexes." (2002). Electronic Theses and Dissertations. Paper 689. https://dc.etsu.edu/etd/689
Copyright by the authors.