Micellar Catalysis of Organic Reactions. 19. Basic Hydrolysis of Carbamates in the Presence of Hydroxy-Functionalized Micelles

Trevor J. Broxton, Roland P.T. Chung

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A number of hydroxy-functionalized micelles were prepared, and their effects on the basic hydrolysis of a number of carbamates are compared. For reactions proceeding by the E1cB mechanism, the intermediate p-nitrophenyl isocyanate was trapped by the hydroxy group of the functional micelles. The efficiency of trapping by the different micelles was compared, and it was found that primary hydroxyl groups were more active than secondary ones. Furthermore, hydroxy groups bonded to the ethyl or propyl groups of detergent molecules 7 and 9 were more effective than those attached to the cetyl chain of 8. The effects of the various micelles on the rate of E1cB hydrolysis and on BAc2 hydrolysis of carbamates and on the decarboxylation of aryl carbamate ions in basic solution were also compared. © 1986, American Chemical Society. All rights reserved.
Original languageEnglish
Pages (from-to)3112-3115
Number of pages4
JournalThe Journal of Organic Chemistry
Issue number16
Publication statusPublished - 1 Jan 1986

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