Premium
Substitution électrophile aromatique. III . Étude cinétique de l'iodo‐déstannylation de dérivés benzéniques substitués et polycycliques aromatiques
Author(s) -
Buchman O.,
Grosjean M.,
Nasielski J.,
Martin R. H.
Publication year - 1964
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19640470703
Subject(s) - chemistry , substituent , electrophilic aromatic substitution , medicinal chemistry , nucleophilic substitution , electrophilic substitution , iodide , electrophile , methanol , nucleophile , reaction rate constant , catalysis , organic chemistry , kinetics , physics , quantum mechanics
Abstract 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.