Add time:08/10/2019 Source:sciencedirect.com
Aryltriethyltin compounds, XC6H4SnEt3, reacted with mercuric acetate in tetrahydrofuran to give arylmercuric acetates and triethyltin acetate. Relative rates of aryl-tin cleavage in these compounds, obtained by competition reactions at 20°, are as follows: p-CH3O, 8.30; p-CH3, 1.76; p-Cl, 0.25; H, 1.00; m-CH3, 1.21; m-CH3O, 0.72; m-Cl, 0.029. Substituent effects are fairly related to the Hammett equation, log kX/kH = −3.5 σ. The results indicate that the reaction is an electrophilic replacement in which a benzenium ion-type intermediate does not participate in the rate-determining step.
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