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Derivatives of ferrocene. VII. Diels Alder reaction of ferrocenylfulvene and its derivatives with N substituted malei- mides

M. Furdík, Š. Toma, J. Suchý, and M. Dzurilla

Komensky University, Bratislava

Abstract: Diels Alder reaction of ferrocenylfulvene, αcyclopentadienylideneethylferrocene, and 1,1'bis(αcyclopentadienylideneethyl)ferrocene with N substituted maleimides and with maleic anhydride gave the following compds. (all endo isomers): anhydride of 7 ferrocenylmethylenebicyclo[1.2.2] 5 heptene 2,3 dicarboxylic acid, yellow, m. 68-9.5° N-Me 7 ferrocenylmethylenebicyclo [1.2.2] 5 heptene 2,3 dicarboximide, red yellow, m. 171-3.5° N Et analog, orange, m. 159-60° N iso-Pr analog, yellow orange, m. 165.5-67° N-allyl analog, yellow, m. 166-8° N Bu analog, red-brown, m. 132-3.5° N Ph analog, yellow, m. 194-5° anhydride of 7 methylferrocenylmethylenebicyclo [ 1.2.2] 5 heptene 2,3 dicarboxylic acid, yellow, m. 159-62° N Me 7 methylferrocenylmethylenebicyclo[ 1.2.2] 5 heptene 2,3 dicarboximide, yellow, m. 162-4° N-Et analog, yellow, m. 148-51° N iso-Pr analog, yellow, m. 142-5° N-allyl analog, yellow, m. 155-8° N-Bu analog, yellow, m. 125-7° N-Ph analog, yellow, m. 166-8° I, yellow, m. 176-80° N,N'dimethyldicarboximide analog yellow, m. 196-200° N,N'diethyl analog, yellow, m. 110-15° N,N'-diisopropyl analog, yellow, m. 135-7°, (diene synthesis in Me2 CO), m. 185-90° (diene synthesis in toluene); N,N'-diallyl analog, yellow, m. 171-4° N,N'di-Bu analog, yellow, m. 134-8° N,N'diphenyl analog, yellow, m. 180-2°, and when run in toluene, m. 247°. Only endo isomers were formed. Ferrocenealdehyde (81% yield) was prepd. from ferrocene by a modification of Vilsmeier's formylation method. Cryst. ferrocenylfulvene was prepd., m. 59-60°, while Osgerby and Pauson ( CA 56, 12939c) obtained it in the oily form.

Full paper in Portable Document Format: 1610a719.pdf (in Slovak)

Chemical Papers 16 (10) 719–740 (1962)