Abstract
The secondary 11 C/ 14 C kinetic isotope effect (KIE) has been determined to 1.010±0.005 for the base-catalyzed rearrangement of 1-methylindene to 3-methylindene isotopically substituted in the methyl group in the solvent benzene at 20°C by using the tertiary amine DABCO as catalyst. The result is discussed in connection with previously reported values of the corresponding primary 2 H and secondary β- 2 H 3 KIEs (5.03 and 1.103, respectively). The isotope effects are consistent with a late TS, structurally close to the ion-pair intermediate postulated in the rate-determining proton abstraction step of the reaction. The influence of hyperconjugation and rehybridization on the magnitude of the secondary carbon KIE is discussed
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