Thallium in organic synthesis. XXIII. Electrophilic aromatic thallation. Kinetics and applications to orientation control in the synthesis of aromatic iodides

EC Taylor, F Kienzle, RL Robey…

Index: Taylor,E.C. et al. Journal of the American Chemical Society, 1971 , vol. 93, # 19 p. 4845 - 4850

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Citation Number: 77

Abstract

Abstract: Aromatic thallation is shown to be a reversible, electrophilic substitution reaction with an energy of activation of 27 kcal/mol and a large steric requirement. The process of thallationfollowed by addition of aqueous potassium iodide represents a simple and facile synthesis of aromatic iodo compounds, and the factors (kinetic, thermodynamic, steric) which control the position of thallation (and hence of iodination) have been systematically ...