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It has been established that the acid hydrolyis of t-butyl acetate proceeds largely by means of alkyl-oxygen fission.1 A unimolecular dissociation is proposed,2 in which transfer of negative charge from the alkyl group to the oxygen atom leads to the formation of the tertiary carbonium ion. Simple primary and secondary acetate esters, on the other hand, acid hydrolyse by acyl-oxygen fission initiated by the bimolecular attack of water at the carbonyl carbon atom.2 The relative acid hydrolysis rates of simple alkyl acetates2 suggest that, for simple carboxylate systems, alkyl-oxygen fission will proceed more rapidly than acyl-oxygen fission. In this connection, we have studied the mode of acid hydrolysis in glycine ester complexes of the form [Co(en)~(glyOR)](C104)~ 334 in which the ester is chelated through the amino nitrogen and carbonyl oxygen atoms. The rates of hydrolysis4-6 in these chelated esters (R = Me > Et > Pri) are c . 106 times faster than the similar hydrolyses of the corresponding N-protonated glycine esters, and it is conceivable that this rate enhancement could reflect a change in mechanism.

Alkyl-oxygen fission in the acid hydrolysis of t-butyl glycinate coordinated to cobalt(III)