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MS (Master of Science)
Date of Award
Committee Chair or Co-Chairs
Hamid S. Kasmai
Ismail O. Kady, Tammy A. Davidson
2-Mercaptobenzenemethaol 14 was prepared by LAH reduction of 2-mercaptobenzoic acid (thiosalicylic acid) in 95% yield. Oxidation of it with PCC afforded 2,2'-dithiobenzaldehyde 15 in 52% yield. A selective reduction of disulfide 15 to 2-mercaptobvenzaldehyde 16 was achieved using triphenylphosphene in MeOH-H2O-DMF solvent mixture. The reaction of 16 with KOH in the presence of 18-crown-6 followed by addition of 1,4-dibromobutane resulted in 4-(o-formylphenthio)butyl bromide 17 which was converted to triphenylphosphonium bromide salt 18 in 75% yield. Wittig cyclization of 18 with K-t-BuO afforded 3,4-dihydro-2H-1-benzthiocin 19 in 71% yield. In an attempt to prepare 2H-1-benzthiocin 13 via dehydrobromination of bromo compound 20, compound 19 was treated with NBS in the presence of catalytic amount of benzoyl peroxide. However, from the complex reaction mixture, only the dibromo compound 21 was isolated and identified.
Thesis - Campus Only
Tang, Mingnam, "Synthesis of 2H-1-Benzthiocin: a Precursor for the Generation of the "4n+2" Pi-electron 1-Benzthiocinide Anion." (2001). Electronic Theses and Dissertations. Paper 50. https://dc.etsu.edu/etd/50
Copyright by the authors.