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Abstract:
Within this thesis, investigation of reactivity of alkenyl thianthrenium salts in nucleophilic substitution reactions was performed. Thianthrenium salts of linear terminal alkenes were found to have three
different types of reactivity towards nucleophiles, depending on the particular nucleophile and the conditions applied (Scheme A1, top); although the ‘Type II’ was already known for other sulfonium
salts, another two reactivities (‘Type I’ and ‘Type III’) were not reported before. Thus, various nucleophiles were tested and classified for each of Type I and Type III, additional mechanistic knowledge for these transformations was gained and based on it, the first round of condition optimizations was undertaken. Also, certain success in reverting reactivity of a Type III nucleophile into Type I and Type II by varying the reaction conditions was achieved (Scheme A1 bottom).
The Type I products with triazoles are stable compounds which are not literature-known. Although improvement of yields for both Type I and Type III products as well as increasing of stereoselectivity for
Type III reactions require additional investigations, the current study has established and summarized
basic knowledge about nucleophilic substitutions on alkenyl sulfonium salts, which might play a role in
the follow-up projects.
