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- W2952267752 abstract "Wittig monoolefination of acenaphthylene-1,2-quinone (1) with ethyl (triphenylphosphoranylidene)acetate yields the o-quinomethane derivative 2 which by 1,3-dipolar cycloaddition reactions with aromatic nitrile oxides affords regioselectively the spiro[acenaphthylene-isoxazoles] 3 and 4. Reaction between 1 and benzonitrile oxide gives the spiro[acenaphthylene-dioxazole] 5 which by treatment with ethyl (triphenylphosphoranylidene)acetate gives compound 6. Reaction between 6 and benzonitrile oxide gives regioselectively the diastereomeric dispiro compounds 7 and 7′. Catalytic hydrogenation of the spiro compounds 6, 7, and 7′ over 10% Pd/C results in the cleavage of the dioxazole ring while cleavage of the isoxazole ring of compound 3 is achieved either by reduction over Raney nickel or by treatment with sodium ethoxide. Reduction of products prepared according Scheme 1 affords the acenaphthylene derivatives 8, 9, and 12 – 15.Darstellung und katalytische Hydrierung von Spiro[acenaphtylen-dioxazolen] und Spiro[acenaphthylen-isoxazolen]Wittig-Olefinierung des Acenapthylen-1,2-chinons (1) mit (Triphenylphosphoranyliden)essigsaure-ethylester fuhrt zum o-Chinomethan-Derivat 3, das in 1,3-dipolaren Cycloadditionen mit aromatischen Nitriloxiden regioselektiv die Spiro[acenaphthylen-isoxazole] 3 und 4 liefert. Reaktion von 1 mit Benzonitriloxid ergibt das Spiro[acenaphthylen-dioxazol] 5, das mit (Triphenylphosphoranyliden)essigsaure-ethylester zu 6 reagiert. Umsetzung von 6 mit Benzonitriloxid liefert regioselektiv die diastereomeren Dispiroverbindungen 7 und 7. Durch katalytische Hydrierung der Spiroverbindungen 6, 7 und 7′ uber 10proz. Pd/C erfolgt Offnung des Dioxazolringes, dagegen ist die Offnung des Isoxazolringes von Verbindung 3 entweder durch Reduktion uber Raney-Nickel oder mit Natriumethylat moglich. Reduktion der nach Schema 1 dargestellten Produkte fuhrt zu den Acenaphthylen-Derivaten 8, 9 und 12–15." @default.
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- W2952267752 date "1987-03-24" @default.
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- W2952267752 title "ChemInform Abstract: Preparation and Catalytic Hydrogenation of Spiro(acenaphthylene-dioxazoles) and Spiro(acenaphthylene-isoxazoles)." @default.
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- W2952267752 doi "https://doi.org/10.1002/chin.198712194" @default.
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