Solvolysis of 2-bromobut-1-en-3-yne (2) and 1-halogenobuta-1,2,3-trienes (3) shows that incorporation of a triple bond in an α-aryl-stabilized vinyl cation system destabilizes the cation owing to a larger inductive effect of the triple bond compared with its π-conjugative effect and that the difference in rates of reaction of (2) and (3a) can be ascribed to a difference in their ground-state energies.
S. Kobayashi, T. Nishi, I. Koyama and H. Taniguchi, J. Chem. Soc., Chem. Commun., 1980, 103 DOI: 10.1039/C39800000103
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