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- W2072101232 abstract "Die Addition von Methylat- oder Cyanid-Ionen an 2 in Dimethylsulfoxid führt über eine elektrocyclische Ringöffnung der intermediär gebildeten Cyclopropyl-Anionen zu den Allyl-Anionen 4, deren Protonierung Gemische der Disäureester 5 und 6 ergibt. Mit Dimethylsulfid, Triphenylphosphan, -arsan und -stiban werden die Ylide 7 – 10 erhalten. – 4a entsteht auch durch Cycloreversion des 1-Pyrazolin-4-yl-Anions 11A, welches aus 1 und Natriummethylat hervorgeht. Hauptprodukt ist jedoch das Pyrazolin 12, dessen N-Methyl-Derivat 12d sich durch photochemische Ringöffnung in das Azomethinimin 14 überführen läßt. 14 wurde durch 1,3-dipolare Cycloaddition an Acetylendicarbonsäure-dimethylester bzw. Fumaronitril abgefangen (15 bzw. 16). 1 liefert mit Cyanid-Ionen über das 1-Pyrazolin-5-yl-Anion nach elektrocyclischer Ringöffnung das Hydrazon 20, dessen Struktur durch Röntgenstrukturanalyse gesichert wurde. Reactions of Spiro[fluorene-9,3′-[3H]pyrazoles] and Spiro[2-cyclopropene-1,9′-fluorenes] with Nucleophiles The addition of methanolate or cyanide ions to 2 in dimethyl sulfoxide gives the allyl anions 4 via electrocyclic ring opening of the cyclopropyl anion intermediate. Protonation of 4 leads to mixtures of the dicarboxylates 5 and 6. With dimethyl sulfide, triphenylphosphane, -arsane and -stibane the ylides 7 – 10 are obtained. – 4a is also formed by cycloreversion of the 1-pyrazolin-4-yl anion 11A, generated from 1 and sodium methanolate. The main product, however, is the pyrazoline 12. The N-methyl derivative 12d is transformed to the azomethinimine 14 by photochemical ring opening. 14 was intercepted by 1,3-dipolar cycloaddition to dimethyl acetylenedicarboxylate and fumaronitrile to yield 15 and 16, respectively. – The reaction of 1 with the cyanide ion leads to the hydrazone 20 formed by electrocyclic ring opening of the intermediate 1-pyrazolin-5-yl anion. The structure of 20 was established by X-ray analysis." @default.
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- W2072101232 date "1984-07-01" @default.
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- W2072101232 title "Reaktionen von Spiro[fluoren-9,3′-[3H]pyrazolen] und Spiro[2-cyclopropen-1,9′-fluorenen] mit Nucleophilen" @default.
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- W2072101232 doi "https://doi.org/10.1002/cber.19841170712" @default.
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