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Synthesis 1996; 1996(6): 711-714
DOI: 10.1055/s-1996-4294
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Straightforward Syntheses of Dienyl- and Diallenylphosphine Oxides from α-Allenols

Christophe Darcel, Christian Bruneau1 , Pierre H. Dixneuf2
  • 1Laboratoire de Chimie de Coordination Organique, URA, CNRS 415, Campus de Beaulieu, Université de Rennes, F-35042 Rennes, France, Fax +33(99)286939
  • 2Laboratoire de Chimie de Coordination Organique, URA, CNRS 415, Campus de Beaulieu, Université de Rennes, F-35042 Rennes, France, Fax +33(99)286939; E-mail dixneuf@univ-rennes1.Fr
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Publication Date:
31 December 2000 (online)

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α-Allenols react with chlorodiphenylphosphine to give (1,3-dien-2-yl)phosphine oxides via a [2,3]-sigmatropic rearrangement. From hepta-2,3-dien-5-yne-1,7-diols, only the propargylic hydroxy group is reactive and diallenylphosphine oxides are selectively formed.

(1,3-dien-2-yl)phosphine oxide - diallenylphosphine oxide - α-allenols - alkynyl α-allenols - sigmatropic rearrangement