Cleavage of benzyl ethers by triphenylphosphine hydrobromide

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/50683

Title:	Cleavage of benzyl ethers by triphenylphosphine hydrobromide
Authors:	Ramanathan,M;Hou,DR
Contributors:	化學學系
Keywords:	3,4-DIMETHOXYBENZYL PROTECTING GROUPS;P-METHOXYBENZYL ETHERS;TRIFLUOROACETIC-ACID;SELECTIVE HYDROGENOLYSIS;MPM 4-METHOXYBENZYL;PEPTIDE CHEMISTRY;ALKYL ETHERS;RANEY-NICKEL;EFFICIENT;DEPROTECTION
Date:	2010
Issue Date:	2012-03-27 18:07:51 (UTC+8)
Publisher:	國立中央大學
Abstract:	Triphenylphosphine hydrobromide was found to cleave the benzyl ethers derived from 1 degrees, 2 degrees alkyl, and aryl alcohols to the corresponding alcohols and benzyltriphenylphosphonium bromide in good yields. Alkene and allyl phosphonium salts were produced from the benzyl ethers with 3 degrees alkyl and allyl groups, respectively. These results indicate that the formation of the product is determined by the relative stability of the carbocationic intermediate. The anhydrous, stoichiometric amount of PPh(3)center dot HBr offers a new and effective method for the deprotection of benzyl ethers. (C) 2010 Elsevier Ltd. All rights reserved.
Relation:	TETRAHEDRON LETTERS
Appears in Collections:	[Department of Chemistry] journal & Dissertation

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