1973
DOI: 10.1039/p29730001719
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Elimination–addition mechanism for the hydrolysis of carbamates. Trapping of an isocyanate intermediate by an o-amino-group

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Cited by 66 publications
(50 citation statements)
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“…However, the effect exerted by the N-substituents of secondary carbamates, e. g. 8 (Fig. 2), on the rate of alkaline hydrolysis is not large, as indicated by the Hammett q value of 0.64 [20], thus suggesting that the estimated drop in the pK a of 3 relatively to that of 2 should reduce the rate of rearrangement; however, it is unlikely this effect could be enough to suppress completely this pathway.…”
Section: Products and Kinetics Of Chemical Hydrolysismentioning
confidence: 90%
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“…However, the effect exerted by the N-substituents of secondary carbamates, e. g. 8 (Fig. 2), on the rate of alkaline hydrolysis is not large, as indicated by the Hammett q value of 0.64 [20], thus suggesting that the estimated drop in the pK a of 3 relatively to that of 2 should reduce the rate of rearrangement; however, it is unlikely this effect could be enough to suppress completely this pathway.…”
Section: Products and Kinetics Of Chemical Hydrolysismentioning
confidence: 90%
“…For example, the carbamate group of compound 3g is expected to be about 2 pK a units less acidic than its counterpart 2a, based on the inductive effects of the substituent on the carbamate NH group [21; see section 3.8]. The rearrangement pathway finds some parallel to the E1cb elimination-addition mechanism operating in the hydrolysis of secondary carbamates in that it also involves the formation of the carbamate conjugate base [20]. However, the effect exerted by the N-substituents of secondary carbamates, e. g. 8 (Fig.…”
Section: Products and Kinetics Of Chemical Hydrolysismentioning
confidence: 99%
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“…These products provide a good mass balance for loss of oxamyl and are consistent with the degradation processes outlined in Scheme 1. Oxamyl oxime forms via a base-catalyzed hydrolysis reaction that occurs independent of either Fe II or TiO 2(s) (E 1 CB mechanism [42]). DMCF is the product of a 2-electron reduction of oxamyl that is coupled with a 1-electron oxidation of two Fe II ions [41].…”
Section: Organic Contaminant Reaction Pathwaysmentioning
confidence: 99%
“…This results in the formation of phenyl carbamate. The carbamate ion is stable in basic medium [23,24].…”
Section: Methodsmentioning
confidence: 99%