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.

G. Bartoli, R. Dalpozzo, A.o De Nino, L. Maiuolo, M. Nardi, A. Procopio, et al. (2004). Cerium (III) Triflate versus Cerium (III) Chloride: Anion Dependence of Lewis Acid Behavior in the Deprotection of PMB Ethers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 0, 2176-2180 [10.1002/ejoc.200400039].

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, et al. (2004). Cerium (III) Triflate versus Cerium (III) Chloride: Anion Dependence of Lewis Acid Behavior in the Deprotection of PMB Ethers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 0, 2176-2180 [10.1002/ejoc.200400039].
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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