Ene Reaction of Triazolinediones with Alkenes. 2. Kinetics and Substituent Effects

Article abstract of DOI:10.1021/jo01305a021

The kinetic measurements for the reaction of 4-substituted-1,2,4-triazoline-3,5-diones (4-R-TD; R=Ph, Me, p-MeOC6H4, p-NO2C6H4) with alkenes have been undertaken.The reactivity of alkenes was found to be very sensitive to substituent effects.The effects of solvent and substituent on TD were small.In the reaction of TD with ene products, side reactions as well as second-step ene reactions were observed.The reactions of 1-alkyl-4-phenyl-1,2,4-triazolidine-3,5-diones were investigated, and the reaction products were isolated.