Cleavage of benzyl ethers by triphenylphosphine hydrobromide

被引：11
|
作者：
Ramanathan, Mani [1 ]
Hou, Duen-Ren [1 ]
机构：
[1] Natl Cent Univ, Dept Chem, Tao Yuan, Taiwan
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 47期
关键词：
3,4-DIMETHOXYBENZYL PROTECTING GROUPS; P-METHOXYBENZYL ETHERS; TRIFLUOROACETIC-ACID; SELECTIVE HYDROGENOLYSIS; MPM; 4-METHOXYBENZYL; PEPTIDE CHEMISTRY; ALKYL ETHERS; RANEY-NICKEL; EFFICIENT; DEPROTECTION;
D O I：
10.1016/j.tetlet.2010.09.065
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 PPh3 center dot HBr offers a new and effective method for the deprotection of benzyl ethers. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6143 / 6145
页数：3
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