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Allyl, methallyl, prenyl, and methylprenyl ethers as protected alcohols: their selective cleavage with diphenyldisulfone under neutral conditions.
Journal article

Allyl, methallyl, prenyl, and methylprenyl ethers as protected alcohols: their selective cleavage with diphenyldisulfone under neutral conditions.

  • Marković D Institute of Chemical Sciences and Engineering, Swiss Federal Institute of Technology, EPFL-BCH, CH-1015 Lausanne, Switzerland.
  • Vogel P
  • 2004-07-30
Published in:
  • Organic letters. - 2004
Alcohols
Allyl Compounds
Ethers
Indicators and Reagents
Sulfones
English Diphenyldisulfone is a mild and efficient reagent for selective cleavage of methylprenyl (2,3-dimethylbut-2-en-1-yl), prenyl (3-methylbut-2-en1-yl), and methallyl (2-methylallyl) ethers. These reaction conditions are compatible with the presence of other protecting groups such as acetals, acetates, and allyl, benzyl, and TBDMS ethers. Exposure of 2,3-dimethylbut-2-en-1-yl and 3-methylbut-2-en1-yl ethers to diphenyldisulfone led to the formation of 2,3-dimethylbuta-1,3-diene and isoprene, respectively. 2-Methylallyl ethers undergo isomerization to 2-methylpropenyl ethers, which are easily hydrolyzed into the corresponding free alcohols and isobutyraldehyde. [reaction: see text]
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://roar.hep-bejune.ch/global/documents/240407
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