MICELLAR CATALYSIS OF ORGANIC-REACTIONS - XXXVIII - A STUDY OF THE CATALYTIC EFFECT OF MICELLES OF 3-HYDROXYMETHYL-1-TETRADECYLPYRIDINIUM BROMIDE ON AMIDE HYDROLYSIS AND NUCLEOPHILIC AROMATIC-SUBSTITUTION

The preparation of 3-hydroxymethyl-1-tetradecylpyridinium bromide and its use as a catalyst of nucleophilic aromatic substitution and also a mide hydrolysis are reported. It was found that the hydroxydehalogenat ion of nitro-activated aryl halides was much faster in these micelles than in the presence of cetyl(2-hydroxyethyl)dimethylammonium bromide. It was concluded that the increased catalysis of nucleophilic aromati c substitution by this micelle was due to a faster decomposition of th e aryl micellar ether which must occur before the phenolate product is released. No such difference in the two micelles was found for amide or thioamide hydrolysis since in these reactions the product amine is produced in the first step of the reaction and decomposition of the ac ylated micelle is not required in the rate-determining step of the rea ction.