Phosphacumulene ylides and phosphaallene ylides are nucleophilic compounds which can add reactants in a variety of ways. Cycloadditions can occur both at the polar C—P ylide bond and at the CC double bond.

Phosphacumulene Ylides and Phosphaallene Ylides [New synthetic methods (19)]

Phosphacumulenylide und Phosphaallenylide sind nucleophile Verbindungen, die ihre Reaktionspartner in verschiedenster Weise addieren konnen. Cycloadditionen sind sowohl an der polaren CP-Ylidbindung als auch an der CC-Doppelbindung moglich.

Phosphacumulenylide und Phosphaallenylide

The chemistry of thioketens

Summary The mechanism of the Wittig reaction is discussed on the basis of recent experimental results. Our observations allow us to predict the stereochemistry of olefines formed by carbonyl olefination with phosphorus ylids or phosphonate anions. Deuterium or tritium may be incorporated into the resulting olefines. Synthetic routes to “symmetric” carotenoids by oxidative dimerisation and the synthesis of “unsymmetric” polyenes using polymeric carriers are discussed. Two approaches to ene-yne-compounds via phosphorus ylids are presented.

Synthesis of polyenes via phosphonium ylids

Die Einwirkung von Natrium-bis(trimethylsilyl)amid (2) auf (Methoxycarbonylmethylen)triphenylphosphoran (1a) bzw. sein Dithioanaloges 1b fuhrt unter β-Eliminierung zu (Triphenylphosphoranyliden)keten (3a) bzw. -thioketen (3b). Die analoge Reaktion von 2 mit den (α-Ethoxyallyliden)-triphenylphosphoranen 8 liefert die stabilen Propadienylidentriphenylphosphorane 9.



Cumulated Ylides, VI. A New Synthesis of (Triphenylphosphoranylidene)ketene, its Thio Analogue, and Stable Propadienylidenetriphenylphosphoranes



Reaction of sodium bis(trimethylsilyl)amide (2) with (methoxycarbonylmethylene)triphenyl-phosphorane (1a) or its dithio analogue 1b leads to β-elimination and formation of (triphenyl-phosphoranylidene)ketene (3a) and -thioketene (3b), respectively. The analogous reaction of 2 with the (α-ethoxyallylidene)triphenylphosphoranes 8 gives rise to the formation of the stable propadienylidenetriphenylphosphoranes 9.

Kumulierte Ylide, VI. Eine neue Synthese des (Triphenylphosphoranyliden)ketens, seines Thioanalogen und stabiler Propadienylidentriphenylphosphorane

Einfache Synthese des Ketenyliden‐triphenylphosphorans und seines Thioanalogen

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Einfache Synthese des Ketenyliden‐triphenylphosphorans und seines Thioanalogen