Allyl, methallyl, prenyl, and methylprenyl ethers as protected alcohols: Their selective cleavage with diphenyidisulfone 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.


Published in:
Organic Letters, 6, 16, 2693-2696
Year:
2004
ISSN:
1523-7060
Keywords:
Note:
Ecole Polytech Fed Lausanne, Swiss Fed Inst Technol, Inst Chem Sci & Engn, BCH, CH-1015 Lausanne, Switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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