Hypervalent Iodine Oxidation of Allenes: Synthesis of 3-Acetoxy-3-alkoxypropynes, 2-Alkoxy-3-tosyloxypropanals and Phenyl-Substituted Propenals and Propenones
- 1 January 1992
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1992 (09) , 847-849
- https://doi.org/10.1055/s-1992-26244
Abstract
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.Keywords
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