Tetrahedron p. 10281 - 10288 (1995)
Update date:2022-08-10
Topics:
Cerichelli, Giorgio
Luchetti, Luciana
Mancini, Giovanna
Savelli, Gianfranco
Observed rate constants (k(obs)) of cyclization of 2-(3-halopropyloxy)phenoxide (halo = bromo, iodo; PhBr7 and PhI7, respectively) in aqueous micelles of N-hexadecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide (1) depend on [1] and [NaOH]. The rate profiles go through a maximum and, at high [1], the catalytic effect is modest. By contrast, k(obs) in aqueous micelles of N-hexadecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium sulfate (2) increases monotonically with increasing surfactant concentration and becomes constant at high [2]. 1H, 13C, and 14N NMR spectra of 1 and 2 show that micelles of 1 and 2 do not differ in dimension and shape and that the average conformations of 1 and 2 are similar.
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