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Introduction of an azido substituent at the α position of benzyl ethers can be achieved by treating them with IN3 in refluxing acetonitrile. Some of the products obtained after 20 min–5 h are given.

A new selective method for the deprotection of benzyl ethers situated next to alcohols in the alpha, beta, or gamma position is presented which uses either NIS or DIB/I2 as a reagent. After initial formation of a hypoiodite intermediate, the reaction is believed to follow a radical pathway to resemble the Hoffman-Loffler-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.

In die α‐Position von Benzylethern lässt sich ein Azidosubstituent einführen, indem diese unter Rückfluss in Acetonitril mit IN3 umgesetzt werden. Einige der nach 20 min bis 5 h erhaltenen Produkte sind gezeigt.