13C and 2H kinetic isotope effects and the mechanism of bromination of 1-pentene under synthetic conditions.
[formula: see text] 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 pi 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.
Merrigan
S R
SR
Department of Chemistry, Texas A&M University, College Station 77843, USA.
Singleton
D A
DA
D000475:Alkenes / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002247:Carbon Isotopes; D002251:Carbon Tetrachloride; D003903:Deuterium; D007700:Kinetics; D012996:Solutions
D000475:Alkenes; D002247:Carbon Isotopes; D012996:Solutions; C410454:1-pentene; D003903:Deuterium; D002251:Carbon Tetrachloride; D001966:Bromine