
TY  - JOUR
A1  - Broxton, TJ 
T1  - Trapping of the Intermediate Formed in the E1cB Hydrolysis of Some Alkyl and Aryl N-(4-Nitrophenyl) carbamates in a Hydroxy Functionalized Micelle
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1985
VL  - 38
IS  - 1
SP  - 77
EP  - 83
KW  - 
UR  - https://doi.org/10.1071/CH9850077 
N2  - The basic hydrolyses of some alkyl and aryl N-(4-nitrophenyl) carbamates in the presence of micelles of cetyl (2-hydroxyethyl) dimethylammonium bromide ( chedab )were studied. For compounds which react by the BAC2 mechanism, verysimilar results were obtained in cetyltrimethylammonium bromide ( ctab ) and in chedab micelles. However, for compounds which react by the E1cB mechanism, the intermediate p- nitrophenyl isocyanate was trapped by the hydroxy group of the functional micelle to form a new carbamate directly bound to the detergent molecules of the micelle. It was shown that this new carbamate decomposed by a BAC2 mechanism. p- Nitrophenyl  isocyanate added to an alkaline solution of chedab gave N-(4-nitrophenyl)- carbamate ion. Thus, the isocyanate has to be generated within the micelle for trapping to occur. The rate of reaction of p-nitrophenyl  isocyanate with OH-/H2O is faster than the rate of solubilization within the micelle. 
ER  -

