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
Full Text: HTML
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 ...
Related Articles:
[Rosen, Brad M.; Wilson, Daniela A.; Wilson, Christopher J.; Peterca, Mihai; Won, Betty C.; Huang, Chenghong; Lipski, Linda R.; Zeng, Xiangbing; Ungar, Goran; Heiney, Paul A.; Percec, Virgil Journal of the American Chemical Society, 2009 , vol. 131, # 47 p. 17500 - 17521]