A Modified Procedure for the Synthesis of Bis(phenylenedioxy)tetrathiafulvalene (BPDO-TTF): an Electron Donor for Charge Transfer Organic Complexes.

<p>Iminium salt dimethyliminium hexafluorophosphate <em><strong>(5)</strong></em>, 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<em><strong>(1)</strong></em> was synthesized from catechol in a strongly alkaline medium. Compound <em><strong>(1)</strong></em> was dichlorinated with SO₂Cl₂ to give 2,3-dichloro-2,3-dihydrobenzo-1,4-dioxin <em><strong>(2)</strong></em>. Subsequent reaction of compound <em><strong>(2)</strong></em> with sodium dimethyldithiocarbamate followed by dehydrochlorination in triethyl amine gave 1,4-Benzodioxin-2-N,N-dimethyldithiocarbamate <em><strong>(3)</strong></em>. Bromination of compound <em><strong>(3)</strong></em> followed by treatment with hexafluorophosphoric acid yielded bromo-dimethyliminium hexafluorophosphate (4). Dehydrobromination of compound <em><strong>(4)</strong></em> by solid phase thermolysis reaction resulted in dimethyliminium hexafluorophosphate <em><strong>(5)</strong></em>. In an effort to prepare BPDO-TTF from a coupling reaction of dithioselenone <em><strong>(7)</strong></em>, the dimethyl iminium salt <em><strong>(5)</strong></em> 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 <em><strong>(5)</strong></em> and trimethyl phosphite but the desired product did not form in a detectable amount.</p>

Name thesis:degree_name

MS (Master of Science)

Level thesis:degree_level

Thesis - restricted

Discipline thesis:degree_discipline

Chemistry

Year dc:date.issued

2002

Author dc:creator

• Biswas, Debanjan

• reduction
• oxidation
• Chemistry
• Physical Sciences and Mathematics

Statement dc:rights

• Copyright by the authors.

Repository record dc:identifier

https://dc.etsu.edu/etd/689

OAI identifier oai:identifier

oai:dc.etsu.edu:etd-1846