Abstract
Abstract The reactions of butatrienyl halides 4 and 5 in aqueous ethanol exclusively gave bis(benzofuranyl)acetylene 6. The first-order kinetics, the leaving group effect, kBr⁄kCl=52, and the Grunwald–Winstein’s m value of ca. 0.5 show that 4 and 5 are solvolyzed by an SN1 mechanism. The intermediate carbenium ion 7 is a new type of ambident vinyl cations.
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