A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers

被引：71

作者：

Iranpoor, Nasser ^{[1
]}

Firouzabadi, Habib ^{[1
]}

Azadi, Roya ^{[1
]}

机构：

[1] Shiraz Univ, Dept Chem, Shiraz 71454, Iran

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 31期

关键词：

triphenylphosphine; ionic liquid; alcohol; trimethylsilyl ether; tetrahydropyranyl ether; halogenation; thiocyanation;

D O I：

10.1016/j.tetlet.2006.05.145

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new diphenylphosphinite ionic liquid (IL-OPPh2) is introduced. This ionic liquid is used as both a reagent and a solvent to convert alcohols and trimethylsilyl and tetrahydropyranyl (THP) ethers into their corresponding alkyl bromides, thiocyanates or isothiocyanates in the presence of Br-2 and SCN- at 80 degrees C. In this ionic liquid, bromination and thiocyanation of alcohols occurs highly selectively in the presence of trimethylsilyl and THP-ethers and also between different classes of alcohols. The use of this ionic liquid allows easy separation of the desired products from the phosphinate by-product. (c) 2006 Published by Elsevier Ltd.

引用

页码：5531 / 5534

页数：4

共 41 条

[31]

Seddon KR, 1997, J CHEM TECHNOL BIOT, V68, P351, DOI 10.1002/(SICI)1097-4660(199704)68:4<351::AID-JCTB613>3.0.CO

[32]

2-4

[33] Development and application of a poly(ethylene glycol)-supported triarylphosphine reagent: Expanding the sphere of liquid-phase organic synthesis [J].