Abstract
AbstractThe preparation of α‐bromo‐p‐aminostyrene (1b) and its solvolysis rates and products have been reexamined in detail. In buffered 50 vol % aqueous dioxane between pH* 13 and 3 the reaction rate is independent of hydrogen ion concentration. The ratio of the solvolysis products, viz. p‐aminoacetophenone (3b) and p‐aminophenylacetylene (5a), however, varies with the pH* and with the buffer concentration.These findings confirm the unimolecular (SN1‐E1) mechanism involving an intermediate vinyl cation. The acid‐catalysed hydration mechanism proposed by Schubert & Barfknecht is thereby excluded.
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