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Derivatives of ferrocene. VIII. Diels-Alder reaction of N-ferrocenylmaleimide with compounds of diene character

M. Furdík, Š. Toma, and J. Suchý

Komensky University, Bratislava

Abstract:   Diels-Alder reaction of N-ferrocenylnaleimide (as the dienophile) with cyclopentadiene, dimethylfulvene, ferrocenylfulvene, α-cyclopentadienylideneethylferrocene, furan, and α-methylfuran was described. These previously unknown bicyclic adducts were prepd.: N-ferrocenylbicyclo[1.2.2]hept-5-ene-2,3-dicarboximide, m. 184°; N-ferrocenyl-7-dimethyhneth-ylenebicyclo[1.2.2]hept-5-ene-2,3-dicarboximide (I), m. 168-70°; N-ferrocenyl-1,4-endoxo-5-cyclohexene-2,3-dicarboximide, m. 155-7°; N-ferrocenyl-l-methyl-l,4-endoxo-5-cyclohexene-2,3-dicarboximide, m. 129-31°; N-ferrocenyl-7-ferrocenylmeth-ylenebicyclo[1.2.2]hept-5-ene-2 3-dicarboximide, m. 192°; and N-ferrocenyl-7-methylferrocenylmethylenebicyclo[1.2.2]hept-5-ene-2,3-dicarboximide, m. 169-70°. All these compds. had the endo-isomeric configuration because the formation of the exo-isomeric configuration was sterically hindered by the ferrocenyl group bound on the imide N. The identity of all these adducts was also detd. by infrared absorption spectra, showing wave-lengths of 1110, 800-900, 1710-20, and 930 cm^-1 The presence of the absorption max. at 618-45 cm^-1 indicates the endo-isomeric form.

Full paper in Portable Document Format: 171a21.pdf (in Slovak)

Chemical Papers 17 (1) 21–30 (1963)