Reaction of bicyclic dienes with 4-substituted-1,2,4-triazoline-3,5-diones

P. Ashkenazi*, D. Ginsburg, G. Scharf, B. Fuchs

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Reaction of 1,2-dihydrophthalic anhydride and several of its imide derivatives, 1,2-dihydrophthalide and 1,2-dihydrophthalan with N-methyl- and N-phenyl-1,2,4-triazoline-3,5-dione affords two configurational families of adducts through attack from both possible directions. Major attack in the first three cases occurs mainly syn- to the hetero-ring but in the two latter cases anti- to it. These results may be explained by invoking stabilization of the transition state in the former cases through secondary orbital overlap and by simple steric effects in the latter.

Original languageEnglish
Pages (from-to)1345-1348
Number of pages4
Issue number11
StatePublished - 1977


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