Isotope effects and heavy-atom tunneling in the Roush allylboration of aldehydes. Academic Article uri icon


  • Intermolecular (13)C kinetic isotope effects (KIEs) for the Roush allylboration of p-anisaldehyde were determined using a novel approach. The experimental (13)C KIEs fit qualitatively with the expected rate-limiting cyclic transition state, but they are far higher than theoretical predictions based on conventional transition state theory. This discrepancy is attributed to a substantial contribution of heavy-atom tunneling to the reaction, and this is supported by multidimensional tunneling calculations that reproduce the observed KIEs.

author list (cited authors)

  • Vetticatt, M. J., & Singleton, D. A

citation count

  • 29

complete list of authors

  • Vetticatt, Mathew J||Singleton, Daniel A

publication date

  • January 2012