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Pyrethrum synergists. XIX. Diels-Alder reaction of isosafrole with N-substituted maleimides

M. Furdík, V. Konečný, and M. Livař

Department of Organic Chemistry, Faculty of Natural Sciences, Komenský University, Bratislava


Abstract: A mixt. of 0.05 mole isosafrole (I) 0.06 mole N-(R-substituted)maleimide, and 50 ml. xylene was refluxed 1.5-96.0 hrs. to give N-(R-substituted) 6,7-methylenedioxy-3-methyl-1,2,3,4-tetrahydronaphthalene-1,2-dicarboximide (II) (R and m.p. given): H, 206-9°; Me, 157-8°; Et, 179-81°; iso-Pr, 209-10°; Bu 139-40°; allyl, 169-70°, Ph, 249°, p-MeC6H4, 250-2°, m-ClC6H4, 150-2°, α-naphthyl, 175-7°, and phenylamino, 213-14°. II were also prepd. by refluxing 1.5 hrs. of 0.019 mole 6,7-methylenedioxy-3-methyl-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic acid anhydride and 0.028 mole of the corresponding aryl amine in 50 ml. toluene. The synergistic effect of II was detd. in mixts. of 5% II, 2.5% pyrethrum and 92.5% acetone. LD50 values are reported on Musca domestica.

Full paper in Portable Document Format: 217a491.pdf (in Slovak)


Chemical Papers 21 (7) 491–500 (1967)

Tuesday, March 31, 2020

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