Isotope effects and the mechanism of deoxygenation of epoxides with dichlorocarbene Academic Article uri icon


  • The deoxygenation of styrene oxide with dichlorocarbene is studied by a combination of isotope effects and theoretical calculations. A normal 13C isotope effect of 1.016 is observed for the -carbon of the styrene oxide but a surprising inverse isotope effect of 0.995 is observed at the -carbon. This is indicative of a highly asynchronous process in which the C-O bond is broken without any progress in the breakage of C-O bond. Theoretical calculations support this interpretation. This coarctate reaction is formally concerted as it avoids involving a high-energy intermediate, but it appears uninfluenced by transition state aromaticity. 2005 Published by Elsevier Ltd.

published proceedings


author list (cited authors)

  • Singleton, D. A., & Wang, Z. H.

citation count

  • 9

complete list of authors

  • Singleton, DA||Wang, ZH

publication date

  • January 2005