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Primary and secondary isotope effects were determined for the reaction of 4-methyl[1,2,4]triazoline-3,5-dione with 2,5-dimethyl-2,4-hexadiene-1,1,1,2',2',2'-d6. The results are consistent with the formation of an aziridinium imide intermediate in equilibrium with an open zwitterion. At higher temperatures, the aziridinium imide prevails and can be either transformed to the ene adduct in a slow step, or trapped by the solvent if the reaction is carried out in methanol. At lower temperatures, the entropically favored open zwitterion is formed preferentially, that either polymerizes in chloroform or can be trapped by methanol.

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Primary and secondary H/D isotope effects in the addition of triazolinedione to 2,5-dimethyl-2,4-hexadiene. Mechanistic insights into the reaction pathways