Aspects of tautomerism. 8. Solvolysis of some pseudo and normal acid chlorides

Abstract

Pseudo acid chlorides derived from levulinic acid and o-benzoyl-benzoic acid, solvolyse in aqueous acetone, aqueous dioxane and aqueous dimethylformamide by a S_N^l process. Their reaction pattern is distinct from that of typical normal acid chlorides, viz.,p-benzoylbenzoyl chloride and fluorene-9-one-1-carboxylic acid chloride, which solvolyse by a S_N² pathway. No evidence for tautomerism could be obtained either between the normal and pseudo forms of the acid chlorides or the derived ion pairs.