Reactions of Carbocations with a Functionalized Hydrophobic Ammonium Ion

Article abstract of DOI:10.1021/jo00372a001

At high pH (2-hydroxyethyl)tri-n-octylammonium bromide and mesylate 2 react readily with Malachite Green or Crystal Violet to give the corresponding ethers.Reaction is promoted by association of the carbocations with clusters of 2 and involves the nucleophilic zwitterion of 2.Reactions are considerably faster than those with OH^- or the cholinate zwitterion, but second-order rate constants in the clusters are lower than in micelles of (2-hydroxyethyl)dimethylhexadecylammonium bromide (1) by a factor of ca. 4.