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Synlett 1991; 1991(2): 123-124
DOI: 10.1055/s-1991-20652
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Sonochemical Generation of Allylic Phosphoranes: An Efficient Route to Conjugated Dienes

Caroline M. R. Low*
  • *James Black Foundation, 68 Half Moon Lane, London SE24 9JE, England
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Publikationsdatum:
07. März 2002 (online)

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Ultrasound was used to promote the deprotonation of various allylic phosphonium salts with butyllithium. The resulting phosphoranes react with benzaldehyde to generate conjugated dienes in excellent yield via the Wittig reaction. The cis/trans ratio of the products was found to be solvent dependent. This is a general route to these useful synthetic intermediates, in contrast to the equivalent thermal reaction which is often erratic and low yielding.