Regioselectivity of the alkylation of ambident anionic species on alumina or in the presence of ‘solid hexamethylphosphoric triamide’

Abstract
C-Alkylation of the acetoacetate anions and of sodium naphthoxide is highly favoured on alumina, while O-alkylation of the acetoacetate anion predominates in tetrahydrofuran in the presence of solid hexamethylphosphoric triamide.

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