Abstract
Diphenylacetylenes are obtained when alkyllithium reagents are added to 3-aryl-2-fluorobenzothiophenes at low temperature. The aromatic ring-opening mechanism involves a nucleophilic addition of the alkyllithium to the sulfur atom of the thiophene. The resulting 2,2-diaryl-l-fluorovinyl anion subsequently undergoes a Fritsch-Buttenburg-Wiechell rearrangement to afford the diphenylacetylene.
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