Isotope effects and the experimental transition state for a prototypical thermal ene reaction
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A complete set of 2H and 13C kinetic isotope effects was determined for the ene reaction of allylbenzene with maleic anhydride. Both bond formation to C1 and hydrogen transfer are implicated by the isotope effects for the rate-limiting step, and a concerted pericyclic transition state is concluded. The observed isotope effects correspond well with those predicted from Becke3LYP transition structures. These structures provide a good model for the steric interactions previously concluded to control selectivity in similar reactions.
author list (cited authors)
Singleton, D. A., & Hang, C.