13C and 2H kinetic isotope effects and the mechanism of bromination of 1-pentene under synthetic conditions. Academic Article

abstract

• [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.

authors

• Singleton, Daniel

author list (cited authors)

• Merrigan, S. R., & Singleton, D. A

citation count

• 4

complete list of authors

• Merrigan, SR||Singleton, DA

publication date

• January 1999

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Alkenes
• Bromine
• Carbon Isotopes
• Carbon Tetrachloride
• Deuterium
• Kinetics
• Solutions

PubMed Central ID

• 10822570

Digital Object Identifier (DOI)

• 10.1021/ol990659d

start page

• 327

end page

• 329

volume

• 1

issue

• 2

URL

• http%3A%2F%2Fdx.doi.org%2F10.1021%2Fol990659d