
%0 Journal Article
%A Broxton, TJ 
%T Trapping of the Intermediate Formed in the E1cB Hydrolysis of Some Alkyl and Aryl N-(4-Nitrophenyl) carbamates in a Hydroxy Functionalized Micelle
%J Australian Journal of Chemistry
%D 1985/01/01
%V 38
%N 1
%P 77-83
%K 
%R https://doi.org/10.1071/CH9850077
%U https://www.publish.csiro.au/paper/CH9850077 
%X 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. 
