Abstract
Cyclohexynes can be generated efficiently from 1-cyclohexenyliodonium salts with acetate or other bases via the E2 and E1 mechanism. The observed regioselectivity of nucleophilic addition to substituted cyclohexynes conforms to the LUMO populations: the less deformed acetylenic carbon is more electrophilic. Cycloheptyne can form by the E1-type elimination via 1,2-rearrangement from cyclohexylidenemethyliodonium salt under very weakly basic conditions.
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