Reactions of triazolinedione with alkenes. A remarkable geminal selectivity

Article abstract of DOI:10.1016/S0040-4039(00)97956-5

The ene reaction of N-Phenyl-1,2,4-triazoline-3,5-dione with alkenes shows a remarkable preference for hydrogen abstraction from the group which is geminal to the larger substituent of the double bond. These results require that the dominant effect in the transition state of the ene reaction is the non-bonded interactions.