Journal of Organic Chemistry p. 3619 - 3624 (1986)
Update date:2022-08-28
Topics:
Cox, Robin A.
Yates, Keith
The excess acidity method has been applied to the hydrolysis reactions of some acylals and thioacylals in aqueous sulfuric acid mixtures.At low acidities, aryl thioacylals (RCH2OCOCH3, R=ArS) react by an A-2 mechanism involving two water molecules, but for aryl acylals (R=ArO) only one is involved.Both undergo a mechanistic switch to an A-1 pathway at high acidity.Linear free energy relationships for both substrates and both mechanisms were found to give acidity-dependent ρ values.Methoxymethyl (R=CH3O) and (methylthio)methyl acetate (R=CH3S) only show the A-1 reaction.Methylene diacetate (R=CH3COO) has two A-1 hydrolysis pathways, one of them A-2-like, involving attack by an internal nucleophile
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