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• W2058746630 endingPage "2658" @default.
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• W2058746630 abstract "Durch entropisch unterstützte intramolekulare Wittig-Reaktion entstehen bei der Umsetzung von α-Ketocarbonsäuren 23 mit Triphenyl[(phenylimino)ethenyliden]phosphoran (1) N-Phenylmaleinisoimide 26 und -imide 29. Die Verbindungen 26 lassen sich mit katalytischen Mengen Natriumazid in 29 umlagern. – Aus γ-Ketosäuren 30 lassen sich über die 3,6-Dioxo-2-(triphenyl-phosphoranyliden)alkananilide 33 3-substituierte 2-Cyclopenten-1-one 37 gewinnen. Analog entstehen aus δ-Ketosäuren 46 3-substituierte 2-Cyclohexen-1-one 49. o-Acylbenzoesäuren 38 lassen sich für R = H mit 1 in das Benzazepindion-Derivat 44 und für R ≠ H in 3-substituierte 1-Oxo-1H-inden-2-carboxanilide 45 überführen. – Ausgehend von Oxocarbonsäuren, die ihre Carbonylfunktion in einem Ring tragen, lassen sich in einfacher Weise 5- und 6-Ringe anellieren. Cumulated Ylides, XVII Synthesis of Cyclic Compounds from Triphenyl[(phenylimino)ethenylidene]phosphorane and Oxocarboxylic Acids – A Novel Method for Anellation By entropically supported intramolecular Wittig reaction from α-keto carboxylic acids 23 with triphenyl[(phenylimino)ethenylidene]phosphorane (1) N-phenylmaleinisoimides 26 and -imides 29 are formed. The compounds 26 can be rearranged into 29 with a catalytic amount of sodium azide. – From γ-keto carboxylic acids 30 3-substituted 2-cyclopenten-1-ones 37 can be derived via the 3,6-dioxo-2-(triphenylphosphoranylidene)alkananilides 33. Analogously, 3-substituted 2-cyclohexen-1-ones 49 are formed from δ-keto carboxylic acids 46. o-Acylbenzoic acids 38, in the case R = H, are converted with 1 into the benzazepinedione derivative 44, and in the case R ≠ H into 3-substituted 1-oxo-1H-indene-2-carboxanilides 45. – Starting from oxo carboxylic acids, possessing the carbonyl function in a ring, five- and six-membered rings can be anellated in a simple way." @default.
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• W2058746630 date "1985-07-01" @default.
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• W2058746630 title "Kumulierte Ylide, XVII. Synthese von cyclischen Verbindungen aus Triphenyl[(phenylimino)ethenyliden]phosphoran und Oxocarbonsäuren – Eine neue Anellierungsmethodik" @default.
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• W2058746630 doi "https://doi.org/10.1002/cber.19851180708" @default.
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