Allyl, methallyl, prenyl, and methylprenyl ethers as protected alcohols: their selective cleavage with diphenyldisulfone under neutral conditions.
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]
Institute of Chemical Sciences and Engineering, Swiss Federal Institute of Technology, EPFL-BCH, CH-1015 Lausanne, Switzerland.
Dean
D
Marković
Pierre
P
Vogel
D000438:Alcohols / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D007202:Indicators and Reagents; D013450:Sulfones / Q000737:chemistry*
D000438:Alcohols; D000498:Allyl Compounds; D004987:Ethers; D007202:Indicators and Reagents; D013450:Sulfones