Reaction of bicyclic dienes with 4-substituted-1,2,4-triazoline-3,5-diones |
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Authors: | P. Ashkenazi D. Ginsburg G. Scharf B. Fuchs |
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Affiliation: | Department of Chemistry, Israel Institute of Technology, Haifa, Israel;Department of Chemistry, Tel Aviv University, Tel Aviv, Israel |
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Abstract: | 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. |
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