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Synergists of pyrethrum. V. Synthesis of endo-cis-and exo-cis-N-substituted-7-isopropylidenebicyclo[1.2.2]hept-5-ene-2,3-dicarboximides

M. Furdík and V. Sutoris

Komensky University, Bratislava


Abstract: The synthesis of N-substituted 7-isopropylidenebicyclo[1.2.2]hept-5-ene-2,3-dicarboximides (I) on the basis of the Diels-Alder reaction of dimethylfulvenes with N-substituted maleimides was described and an exptl. proof of a configuration of endo and exo isomers of corresponding derivs. given. Structural changes on the skeleton of compds. of this type by hydrogenation of isolated double bonds in the position 5 and by the redn. of both carbonyls on methylene groups were described. It was proven exptl. that the formation of the exoisomer of the N-Ph deriv. was not possible owing to steric effects. I were not effective as insecticides but were effective as synergists in mixts. with pyrethrum. This effect was decreased by the hydrogenation of the cyclic double bond in the 5 position and increased by the redn. of both carbonyls on methylene groups. Among the substituents on N, allyl, Et, and iso-Pr had favorable effects. Exoisomers of higher potential energy had a higher effect than endoisomers, contrary to adducts of furan with N-substituted maleimides, where endoisomers of higher potential energy show a higher effect.

Full paper in Portable Document Format: 148a564.pdf (in Slovak)


Chemical Papers 14 (8) 564–580 (1960)

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