Imide und imid‐ähnliche Systeme, XII Wittig‐Olefinierungen von N‐brückenkopf‐bicyclischen Imiden

Flitsch, Wilhelm; Müter, Bernhard

doi:10.1002/cber.19711040925

Cited by 8 publications

(1 citation statement)

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“…Dagegen reagiert N-Methylglutarimid bei 200°C nur mit 1 Iproz. Ausbeute unter Bildung von (I-Methyl-6-0x0-2-piperidiny1iden)essigsaure-ethylester 13).…”

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Thiocarbonyl‐Olefinierung, II. Einige präparative Anwendungen der Reaktion von N‐(Thioacyl)urethanen und deren Vinylogen mit resonanzstabilisierten Phosphor‐Yliden

et al. 1979

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Thiocarbonyl Olefination, 11'). -Some Preparative Uses of the Reaction of N-(Thioacy1)-urethanes and their Vinylogues with Resonance-stabilized Phosphorus Ylides**'In contrast to the corresponding oxygen analogues, dithioglutarimides and N-(thioacy1)urethanes react readily with resonance-stabilized phosphorus ylides, yielding triphenylphosphane sulfide and forming a C = C bond with the carbon atom of the thiocarbonyl group. Most likely, the mechanism of this reaction parallels that of the Wittig olefination of carbonyl compounds. Under the same conditions, the (6-thioxo-2-piperidiny1idene)acetates 2a and 2h react with methyl (triphenylphosphorany1idene)acetate to yield a mixture of the corresponding bis-enamine 9a or 9h and (3-oxo-2,3,4,5,6,7-hexahydrothieno[2,3-b]pyridin-6-ylidene)acetate 10a or 10 b, respectively.

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“…Dagegen reagiert N-Methylglutarimid bei 200°C nur mit 1 Iproz. Ausbeute unter Bildung von (I-Methyl-6-0x0-2-piperidiny1iden)essigsaure-ethylester 13).…”

unclassified