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pi-Arene/Metal Binding: An Issue Not Only of Structure but Also of Reactivity

A trimethyl-, triethyl-, or triisopropylsilyl group attached to the meta position of toluene retards the rate of permutational H/metal interconversion with butyllithium in the presence of K tert-butoxide by factors of 1.7, 3, and 7, resp. Although remote from the reaction center, the substituents sterically impede the coordination of K to the arene electron sextet. p-Arene/metal bonding may play a major role in modulating chem. and, by extension, biochem. reactivity. [on SciFinder (R)]

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