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

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

Organic Letters 6(16): 2693-2696

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]

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Accession: 048210946

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PMID: 15281746

DOI: 10.1021/ol049135q

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