The development of new and efficient methods for the formation of C—S bonds is of significant importance. Various methods have been developed that describe the formation of C—S bonds; however, most of these processes require that the substrates be activated before any reactivity is achieved. Robertson et al. described a facile two-step process for the formation of C—S bonds starting from two alcohols, which was then applied to an intramolecular process for the formation of chiral tetrahydrothiophenes (THTs). In an effort to expand the scope of the intramolecular C—S bond-forming process so that the THT moiety can be accessed from other common functional groups this area shall be thoroughly investigated. The development of a synthetic method that describes the synthesis of 2-subsitituted THTs shall be fully explored due to the biological significance of this structural motif. As noted in the literature, sulfides have been shown to possess anticarcinogenic, antithrombotic, and antitumorigenic properties. The synthesis began from 5-bromo-1-pentene, which was readily converted to the common intermediate O,O-diethyl S-(3-(oxiran-2-yl)propyl) phosphorothioate. O,O-diethyl S-(3-(oxiran-2-yl)propyl) phosphorothioate was treated with various aromatic amines to synthesize the corresponding alcohols, which were then converted to the desired 2-substituted tetrahydrothiophenes under NaH conditions.

Accessing a library of 2-substituted tetrahydrothiophenes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.