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Substitution électrophile aromatique. III. Étude cinétique de l'iodo‐déstannylation de dérivés benzéniques substitués et polycycliques aromatiques

par Buchman, Ouri ;Grosjean, Mireille ;Nasielski, Jacques ;Martin, Richard
Référence Helvetica chimica acta, 47, 7, page (1679-1688)
Publication Publié, 1964

Article révisé par les pairs

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Résumé :

The rate of the reaction between iodine and a series of substituted phenyltri‐ methyltins in methanol has been determined and activation parameters estimated. The rates correlate well with the σ+ substituent constants, showing that the iodo‐ destannylation is an aromatic electrophilic substitution. The reaction shows interesting salt effects whose magnitude depends on the substituent, suggesting a rather polar transition state. The rates show no catalysis by iodide ions, implying that nucleophilic attack on tin is kinetically non‐significant. Copyright © 1964 Verlag GmbH & Co. KGaA, Weinheim