Cerium (III) triflate versus cerium (III) chloride: Anion dependence of lewis acid behavior in the deprotection of PMB ethers

…, R Dalpozzo, AD Nino, L Maiuolo…

Index: Bartoli, Giuseppe; Dalpozzo, Renato; De Nino, Antonio; Maiuolo, Loredana; Nardi, Monica; Procopio, Antonio; Tagarelli, Antonio European Journal of Organic Chemistry, 2004 , # 10 p. 2176 - 2180

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Citation Number: 21

Abstract

Abstract Cerium (III) triflate deprotects p-methoxybenzyl ethers of simple alcohols better than the cerium (III) chloride/sodium iodide system. It can be used in 1% M instead of equimolecular amounts, giving better yields. Aromatic alcohols rearrange, but the addition of a scavenger overcomes this drawback. Unfortunately, unsaturated alcohols are deprotected with decomposition, probably due to side electrophilic additions to double bonds. A ...