Abstract
The ene reaction of 4-methyl-1,2,4-triazoline-3,5-dione (MTAD) with phorone-d(6) (5-d(6)) shows an inverse beta-secondary isotope effect and with mesityl oxide-d(3) (7-d(3)) proceeds with 93% syn selectivity. These results are consistent with a mechanism involving the formation of an aziridinium imide intermediate in the rate-determining step. An open biradical or dipolar intermediate is excluded by them.
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