Iodination Reactions of Ketones in the Reversed Micellar Systems of Dodecylammonium Propionate in Hexane

The iodination reactions of ketones in the reversed micellar systems of dodecylammonium propionate (DAP) in hexane were studied at 25.0 °C in relation to the enzymatic function of aldolase or enolase. The reaction rate in the DAP reversed micellar system is 106–107 times greater than that in the system without DAP, 100 times greater even in comparison with that in DAP aqueous system at pH 6.8. As in the ammonium ion catalyzed reaction in aqueous media, the reaction in the presence of DAP proceeds via ketimine formation between ammonium groups of DAP and acetone and subsequent enolization of ketimine to enamine, which reacts very rapidly with iodine. The catalytic effect of DAP reversed micellar system in each reaction step was discussed. Further, this reversed micellar system shows a marked selectivity for acetone as compared with higher analogs.