Kinetic and isotopic exchange data employing H2O18 are presented to establish the bimolecular alkaline hydrolysis with alkyol–oxygen fission (BAL2) for the highly hindered ester methyl 2,4,6-tri-t-butylbenzoate. Methyl 2-methyl-4,6-di-t-butylbenzoate also cleaved predominately by alkyl–oxygen fission. Other hindered esters, methyl 2,4,6-trimethylbenzoate and methyl 2,5-di-t-butylbenzoate, hydrolyzed by the usual acyl–oxygen fission.
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Barclay et al. (1962) studied this question.
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