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Synthesis 1988; 1988(1): 49-53
DOI: 10.1055/s-1988-27461
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Kumulierte Ylide XIX.1 Acylphosphoniumylide durch kettenverlängernde Difunktionalisierung von Grignard-Verbindungen mit Ketenylidentriphenylphosphoran. Anwendung zur Synthese (E)-α,β-ungesättigter-Ketone und der Königinsubstanz

Hans Jürgen Bestmann* , Martin Schmidt, Rainer Schobert
  • *Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestraße 42, U-8520 Erlangen, Federal Republic of Germany
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Publikationsdatum:
12. September 2002 (online)

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Cumulated Ylides XIX.1 Chain-lengthening Difunctionalization of Grignard Compounds by Reaction with Ketenylidenetriphenylphosphorane. A New Route to (E)-α,β- Unsatured Ketones and the Queen Substance2 The reaction of Grignard compounds with ketenylidenetriphenylphosphorane and subsequent hydrolysis yields 2-oxoalkylidenetriphenylphosphoranes. The latter undergo Wittig reaction, whereby (E-α,β-unsaturated ketones are obtained. An application of this strategy to the synthesis of carbonyl homologues of Lepidoptera pheromones and the queen substance is shown.