CYCLIZATION OF 2-(3-HALOPROPYLOXY)PHENOXIDE IONS IN FUNCTIONALIZED SURFACTANTS

Observed rate constants (k(obs)) of cyclization of 2-(3-halopropyloxy) phenoxide (halo = bromo, iodo; PhBr7 and Ph17, respectively) in aqueou s micelles of -hexadecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromi de (1) depend on [1] and [NaOH]. The rate profiles go through a maximu m and, at high [1], the catalytic effect is modest. By contrast, k(obs ) in aqueous micelles of -hexadecyl-N-(2-hydroxyethyl)-N,N-dimethylamm onium sulfate (2) increases monotonically with increasing surfactant c oncentration and becomes constant at high [2]. H-1, C-13 and N-14 NMR spectra of 1 and 2 show that micelles of 1 and 2 do not differ in dime nsion and shape and that the average conformations of 1 and 2 are simi lar.