Epoxidation of alkenes using HOF•MeCN by a continuous flow process

被引:30
作者
McPake, Christopher B. [1 ]
Murray, Christopher B. [2 ]
Sandford, Graham [1 ]
机构
[1] Univ Durham, Dept Chem, Durham DH1 3LE, England
[2] Aldermaston, AWE, Reading RG7 4PR, Berks, England
关键词
ELEMENTAL FLUORINE; MICROREACTORS; CHEMISTRY;
D O I
10.1016/j.tetlet.2008.12.073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Continuous flow methodology is described which allows the in situ generation of the highly effective oxidising agent HOF center dot MeCN from fluorine and wet acetonitrile and immediate reaction with alkenes to afford epoxides in high yield. The HOF center dot MeCN continuous flow oxidising system provides an environmentally benign process that is suitable for large scale synthesis and is atom efficient, because the only by-product is hydrogen fluoride which, in principle, could be recycled to produce fluorine by electrolysis. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved
引用
收藏
页码:1674 / 1676
页数:3
相关论文
共 13 条
[1]   Elemental fluorine - Part 16. Versatile thin-film gas-liquid multi-channel microreactors for effective scale-out [J].
Chambers, RD ;
Fox, MA ;
Holling, D ;
Nakano, T ;
Okazoe, T ;
Sandford, G .
LAB ON A CHIP, 2005, 5 (02) :191-198
[2]   Microreactors for oxidations using fluorine [J].
Chambers, RD ;
Holling, D ;
Rees, AJ ;
Sandford, G .
JOURNAL OF FLUORINE CHEMISTRY, 2003, 119 (01) :81-82
[3]   Elemental fluorine - Part 13. Gas-liquid thin film microreactors for selective direct fluorination [J].
Chambers, RD ;
Holling, D ;
Spink, RCH ;
Sandford, G .
LAB ON A CHIP, 2001, 1 (02) :132-137
[4]   Microreactors for elemental fluorine [J].
Chambers, RD ;
Spink, RCH .
CHEMICAL COMMUNICATIONS, 1999, (10) :883-884
[5]  
CHAMBERS RD, 2002, Patent No. 02108090
[6]  
Ehrfeld W., 2000, Microreactors: new technology for modern chemistry, DOI DOI 10.1002/3527601953
[7]   The application of micro reactors to synthetic chemistry [J].
Haswell, SJ ;
Middleton, RJ ;
O'Sullivan, B ;
Skelton, V ;
Watts, P ;
Styring, P .
CHEMICAL COMMUNICATIONS, 2001, (05) :391-398
[8]   Oxidation of alkenes by oxodiperoxomolybdenum: Trialkyl(aryl)phosphine oxide complexes [J].
Kiraz, Christine I. Altinis ;
Mora, Luis ;
Jimenez, Leslie S. .
SYNTHESIS-STUTTGART, 2007, (01) :92-96
[9]  
MURRAY CB, 2008, Patent No. 08161705
[10]   Elemental fluorine and HOF-CH3CN in service of general organic chemistry [J].
Rozen, S .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (12) :2433-2447