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Substitution électrophile aromatique. IV. Effets stériques dans la réaction d'iodo‐démétallation de dérivés organostanniques aromatiques

par Buchman, Ouri ;Grosjean, Mireille ;Nasielski, Jacques ;Wilmet‐Devos, B.;Martin, Richard
Référence Helvetica chimica acta, 47, 7, page (1688-1695)
Publication Publié, 1964

Article révisé par les pairs

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Résumé :

Aromatic organo‐tin compounds ArSnR3 have been synthesized with R = n‐butyl and R = i‐propyl. Increased bulk of the leaving group results in lower reactivity towards iodine, showing appreciable interactions between the incoming and leaving groups. A peri hydrogen atom induces a secondary steric acceleration, suggesting that the ground state for large R3Sn substituents in 1‐naphthyl systems is strained. This agrees with previous reports by EABORN et coll. [14] relating to the corresponding silicon and germanium compounds. Copyright © 1964 Verlag GmbH & Co. KGaA, Weinheim