engleski

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.

alkenes; isomerization; organocatalysts

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