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Synergists of pyrethrum. VI. Synthesis of endo-cis-Nsubstituted 7-diphenylmethylenebicyclo[1.2.2]hept-5-ene-2,- 3-dicarboximides

M. Furdík and V. Sutoris

Komensky University, Bratislava

 

Abstract: cf. CA 55, 16444c. By Diels-Alder reaction of diphenylfulvene with N-substituted maleimides were synthesized N-Me, N-Et, N-iso-Pr, N-allyl, N-Bu, N-Ph, and N-benzyl derivs. of 7-diphenylmethylenebicyclo[1.2.2]hept-5-ene-2,3-dicarboximides. It was proven exptl. that these compds. were endo isomers. The formation of exo isomers was prevented by the steric effect of 2 voluminous Ph groups bound on the endo bridge. M.ps. of the following N-substituted compds. were given: Me, 183°; Et, 118°; iso-Pr, 200°; allyl, 168°; Bu, 181°; Ph, 230°; benzyl, 128°. These endo isomers were isolated by catalytic (Pd-BaSO4) hydrogenation of the double bond in the 5-position of the corresponding dihydro derivs. (same data): 133°; Et, 134°; iso-Pr, 205°; allyl, 188°; Bu, 168°; Ph, 273°; benzyl, 121°. Analogously, more endo isomers were prepd. by redn. (LiAlH4) of both carbonyl groups to methylene groups (same data): Me,-(n20D 1.6010); Et, 75°; iso-Pr, 68°; allyl, - (n20D 1.6002); Bu, - (n20D 1.5869); Ph, 139°; benzyl, - (n20D 1.5840).

Full paper in Portable Document Format: 153a173.pdf (in Slovak)

 

Chemical Papers 15 (3) 173–180 (1961)

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