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87 The experimental evidence of the rates of lactonization of various hydroxy-carboxylic acids used to form the basis of orbital steering88 is questionable since the structures of some of the acids were incorrectly ~ t a t e d . 91 Reactions of Acids and their Dwivutives 31 The pH-rate profiles for the hydrolysis of phenyl N-(0-carboxypheny1)carbamate(23) and its N-methyl derivative show a pH-independent region between pH 4 and 10. The presence of the o-carboxy-group enhances phenol release by ca.
Hydrolysis in 180-enriched water results in incorporation of label in both the keto-carbonyl and the carboxyl group. 25. An ElcB mechanism (equation I ) , similar to that suggested for phenolic leaving groups,sl was suggested. Remtions of Acids and their Derivatives HO- + PhNHCOX 7HZO + PhNCOX - 29 Ph-N&=O + X- (1) Products It was estimated that the change-over from elimination ElcB to substitution occurs when the pK, of the leaving group exceeds ca. 61 The rate constants for the acid-catalysed hydrolysis of 4-chlorobenzamides do not correlate with the Bunnett or BunnettOlsen criteria.
Reactions of Acids und their Derivatives 45 It is suggested that the alkaline hydrolysis of a-hydroxyimino-p-nitrobenzylphosphates, phosphonates and phosphinates (55) (X is alkyl or alkoxy) proceeds by intramolecular attack by the oximinate function on phosphorus, to give a pentacovalent intermediate. Fission of the latter and a subsequent Lossen rearrangement gives pnitroaniline and the parent phosphorus acid. 283 The pH-rate profiles for hydrolysis of 2-pyridylethyl and 2-pyridylpropyl phosphate are bell-shaped with maxima a t pH 2-3.