Abstract
The reactions of 2,6-di-tert-butyl-4-methoxyphenyl 2-methoxybenzoate 1a with several organolithium and -magnesium reagents are found to give the methoxy-substitution products 2 and/or the conjugate addition products to the benzoate ring ( 3 and 4 ), preferring the latter products at the expense of the former with the increase of the electron-donating ability of the carbonion species. A SET mechanism is proposed for the conjugate addition. Reactions of benzoates with organolithium and -magnesium reagets lead to nucleophilic aromatic substitution and/or conjugate addition.
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