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Synthesis 1992; 1992(9): 847-849
DOI: 10.1055/s-1992-26244
short paper
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Hypervalent Iodine Oxidation of Allenes: Synthesis of 3-Acetoxy-3-alkoxypropynes, 2-Alkoxy-3-tosyloxypropanals and Phenyl-Substituted Propenals and Propenones

Robert M. Moriarty* , Thomas E. Hopkins, Radhe K. Vaid, Beena K. Vaid, Stuart G. Levy
  • *University of Illinois at Chicago, Chemistry Department P.O. Box 4348, M/C 111, Chicago, Illinois 60680, USA
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Publication Date:
17 September 2002 (online)

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1-Alkoxyallenes yield 3-acetoxy-3-alkoxypropynes upon oxidation with [(diacetoxy)iodo]benzene at - 78°C in dichloromethane. Treatment with [hydroxy(tosyloxy)iodo]benzene under similar conditions gives 2-alkoxy-3-tosyloxypropanals. Phenyl-substituted propenals and propen-1-ones are obtained from the treatment of phenyl-substituted alienes with [hydroxy(tosyloxy)iodo]benzene in dichloromethane at - 78°C.

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