Abstract
Cycloaddition of TCNE to 2-methyl-1′,1′,1′-d 3-5-methyl-2,4-hexadiene-1,1,1-d 3 (DMHD-d 6) shows a substantial secondary isotope effect, which depends on solvent polarity. This remote ε- secondary isotope effect is a result of hyperconjugation in the dipolar intermediate which is formed in the rate determining step.
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