13C and 2H kinetic isotope effects and the mechanism of bromination of 1-pentene under synthetic conditions
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(equation presented) The 13C and 2H kinetic isotope effects for the bromination of 1-pentene with Br2 in CCl4 were determined and interpreted with the aid of calculationally predicted isotope effects. The isotope effects observed are consistent with rate-limiting bromonium ion formation and do not fit with either rate-limiting production of a π complex or reaction of a reversibly formed bromonium ion. This rules out some of the mechanistic complexities suggested for other brominations, though the identity of the brominating reagent(s) under these synthetic conditions remains uncertain.
author list (cited authors)
Merrigan, S. R., & Singleton, D. A.