Reactions in Microemulsion Media. Nucleophilic Substitution Reactions of Benzyl and p-Alkylbenzyl Chlorides

Article abstract of DOI:10.1021/jo00197a012

A kinetic and synthetic study of nucleophilic displacement reaction of bromide ion with benzyl chloride (1a) and its p-ethyl-substituted (1b) and p-n-dodecyl-substituted (1c) analogues has been performed in microemulsions prepared from combinations of a 1.23:1 (w/w) mixture (S) of cetyltrimethylammonium bromide (CTABr) and 1-butanol, a 1:5 (w/w) KBr-H2O solution (W), and hexane (O).The rates of reaction decreased differentially with increasing hexane content at a constant ratio of S:W to indicate that the interphase was the microemulsion reactive site.For microemulsion with respect to aqueous micellar and aqueous ethanol reaction media, solubilization of substrate was higher, initial reaction rates were comparable or slightly less, and overall conversions were greater.