SOLVOLYSIS OF BUTATRIENYL HALIDES: EVIDENCE OF AN AMBIDENT VINYL CATION
- 5 February 1977
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 6 (2) , 163-166
- https://doi.org/10.1246/cl.1977.163
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.This publication has 8 references indexed in Scilit:
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