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Degree Name

MS (Master of Science)

Program

Chemistry

Date of Award

12-2001

Committee Chair or Co-Chairs

Hamid S. Kasmai

Committee Members

Ismail O. Kady, Tammy A. Davidson

Abstract

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.

Document Type

Thesis - Campus Only

Copyright

Copyright by the authors.

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