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Title: Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes
Authors: Xiao, Yongjun
Keywords: DRNTU::Science::Chemistry::Organic chemistry
Issue Date: 2008
Abstract: During the course of study on the nucleophilic substitution reaction at an sp2 carbon in the Narasaka group, a unique four-membered ring formation was realized by intramolecular nucleophilic vinylic substitution of a thiolate moiety. To generalize this 2-alkylidenethietane formation and to get more mechanistic information, synthesis of 2-alkylidenethietanes were examined by using this newly developed synthetic methodology. It was found that 2-alkylidenethietanes were oxidized to 2-alkylidenethietan- 1-oxides by treatment with m-CPBA, which has a unique structure with a strained four-membered ring, an exo double bond, and a sulfinyl group. Accordingly, the transformation of 2-alkylidenethietan-1-oxides were investigated. Incidentally, it was discovered that the treatment of 2-alkylidenethietan-1-oxides with p-toluenesulfonic acid afforded the unexpected thiophenes. The thiophene formation was extensively studied in this MSc’s thesis.
Schools: School of Physical and Mathematical Sciences 
Fulltext Permission: restricted
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

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