HARD ACID AND SOFT NUCLEOPHILE SYSTEM - NEW EFFICIENT METHOD FOR REMOVAL OF BENZYL PROTECTING GROUP

被引：186

作者：

FUJI, K ^{[1
]}

ICHIKAWA, K ^{[1
]}

NODE, M ^{[1
]}

FUJITA, E ^{[1
]}

机构：

[1] KYOTO UNIV,INST CHEM RES,UJI,KYOTO 611,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 10期

关键词：

D O I：

10.1021/jo01324a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aliphatic and aromatic benzyl ethers have been easily cleaved on treatment with a hard acid, boron trifluoride etherate, and a soft nucleophile, EtSH or ethanedithiol, to give parent alcohols and phenols, respectively. Competitive debenzylation experiments demonstrated that the coordination of a hard acid (pulling factor) is more important than the nucleophilic attack of a soft nucleophile to the carbon atom (pushing factor) in this reaction. © 1979, American Chemical Society. All rights reserved.

引用

页码：1661 / 1664

页数：4

共 15 条

[1] THE ELBS PERSULPHATE OXIDATION OF PHENOLS, AND ITS ADAPTATION TO THE PREPARATION OF MONOALKYL ETHERS OF QUINOLS [J].