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 thisdrawback. Unfortunately, unsaturated alcohols are deprotected with decomposition, probably due to side electrophilic additions to double bonds. A comparison between the mechanisms of cerium triflate and cerium chloride is reported.

Cerium (III) Triflate versus Cerium (III) Chloride: Anion Dependence of Lewis Acid Behavior in the Deprotection of PMB Ethers

BARTOLI, GIUSEPPE;
2004

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 thisdrawback. Unfortunately, unsaturated alcohols are deprotected with decomposition, probably due to side electrophilic additions to double bonds. A comparison between the mechanisms of cerium triflate and cerium chloride is reported.
2004
G. Bartoli; R. Dalpozzo; A.o De Nino; L. Maiuolo; M. Nardi; A. Procopio; A. Tagarelli
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/8610
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