Effect of Multiple Field Assistance with Reversed Micelles on the Decarboxylation of 6-Nitro-1,2-benzisoxazole-3-carboxylate

Publisher Website
Google Scholar
Abstract
Decarboxylation reaction of 6-nitro-1,2-benzisoxazole-3-carboxylate (1) in cationic and anionic reversed micelles has been investigated with particular attention to the microenvironmental effect, such as microviscosity, micropolarity, and microactivity, in the specific and restricted reaction field as provided by reversed micelles. In 0.20 M CTAC/0.32 M H2O/CHCl3 reversed micelles, the reaction was accelerated about 1300-fold compared with that in bulk aqueous solution. Of various surfactant aggregate systems such as aqueous micelle, bilayer, and reversed micelle, the cationic reversed micelle could provide the most effective reaction field for the present decarboxylation reaction. This reaction is never accelerated in an anionic aqueous micelle. However, in the anionic AOT reversed micelle, the reaction was apparently accelerated by both lowering the micropolarity and increasing the microviscosity around the substrate. The unique rate enhancement for the decarboxylation reaction of 1 provided by reversed micelles was interpreted in terms of the “multiple field assistance.”