Abstract
Rate coefficients have been determined by a spectrophotometric method for the acid-catalysed methanolysis at 30° of (1,2-epoxyethyl)benzene and of XC6H4·[graphic omitted] (X =p-Br, m- or p-Cl, m-Me, m-MeO, or m- or p-NO2), and for the acid-catalysed ethanolysis, propan-1-olysis, and butan-1-olysis at 30° of similar epoxides with X = H, m-Cl, m-Me, or p-NO2. Alcoholysis is unidirectional giving the abnormal products (primary alcohols) only.The values of the entropy of activation (ΔS‡) for methanolysis are in the range –12·3 to –13·5 cal mol–1 K–1, and the Hammett ρ-values for abnormal attack are between –3·8 and –4·2, which suggests a consistency of mechanism. The reaction is discussed in terms of a borderline A2 mechanism.A slow acid-catalysed reaction has also been discovered for the epoxides XC6H4·[graphic omitted] (X = H, p-Br, p-Cl, or m- or p-Me), which is regarded as a rearrangement of the epoxide to the corresponding arylacetaldehyde. With four other epoxides (X =m-Cl, m-MeO, or m- or p-NO2) this reaction was not detected.
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