Date of Award
Chemistry and Biochemistry
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This thesis presents the synthesis of terminal alkynes from (Z)-iodoalkenes using a novel route via E2-elimination. The introduction reviews some of the most popular currently used methods for alkyne synthesis, with a mechanistic overview and an evaluation of the scope of their use and their limitations. An efficient method to convert (Z)-iodoalkenes using a mild base, tetrabutyl ammonium fluoride (TBAF), is then described. Several (Z)-iodoalkene derivatives were prepared from the corresponding aldehyde under standard Wittig conditions. The methodology has been successfully applied for the synthesis of several aromatic acetylenes in good to excellent yields.
Beshai, Mira M., "Synthesis of alkynes via elimination of (Z)-alkenyl iodides using tetrabutylammonium fluoride" (2008). Electronic Theses and Dissertations. 8206.