A New Method for the Deprotection of Benzyl Ethers or the Selective Protection of Alcohols

A new selective method for the deprotection of benzyl ethers situated next to alcohols in the α, β, or γposition is presented which uses either NIS or DIB/I2as a reagent. After initial formation of a hypoiodite intermediate, the reaction is believed to follow a radical pathway to resemble the Hoffman‐Löffler‐Freytag reaction. The formation of the intermediate hypoiodite is suggested on the basis of NMR studies. Depending on the substrate, the corresponding benzylidene derivatives or diols are isolated.