Studies on the B(AL)2 mechanism for esther hydrolysis

Article abstract of DOI:10.1139/v93-230

The preparation and alkaline hydrolysis of ¹⁸O-methyl 2,2-dimethylpropanoate and ¹⁸O-methyl triphenylacetate are reported. From mass spectral analysis of the carboxylic acid products, it is concluded that the former substrate is hydrolyzed exclusively by the B(AC)2 mechanism, whereas the latter substrate proceeds 95% by the B(AC)2 mechanism and 5% by the B(AL)2 mechanism. The balance between these two mechanisms is discussed.