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

Bartoli Giuseppe | Zendy; Dalpozzo Renato | Zendy; Nino Antonio De | Zendy; Maiuolo Loredana | Zendy; Nardi Monica | Zendy; Procopio Antonio | Zendy; Tagarelli Antonio | Zendy

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

Author(s) -

Bartoli Giuseppe,

Dalpozzo Renato,

Nino Antonio De,

Maiuolo Loredana,

Nardi Monica,

Procopio Antonio,

Tagarelli Antonio

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400039

Subject(s) - chemistry , cerium , trifluoromethanesulfonate , sodium iodide , chloride , iodide , electrophile , lewis acids and bases , polymer chemistry , organic chemistry , medicinal chemistry , catalysis

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 comparison between the mechanisms of cerium triflate and cerium chloride is reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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