Synthesis of hydroximoyl chlorides from aldoximes and benzyltrimethylammonium tetrachloroiodate (BTMA ICl4)

被引：49

作者：

Kanemasa, S ^{[1
]}

Matsuda, H

Kamimura, A

Kakinami, T

机构：

[1] Kyushu Univ, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan

[2] Kyushu Univ, Dept Mol Sci & Technol, Interdisciplinary Grad Sch Engn Sci, Kasuga, Fukuoka 8168580, Japan

[3] Yamaguchi Univ, Fac Engn, Dept Appl Chem, Ube, Yamaguchi 7558611, Japan

[4] Ube Natl Coll Technol, Dept Chem & Biol Engn, Ube, Yamaguchi 7558555, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 08期

关键词：

hydroximoyl chlorides; benzyltrimethylammonium tetrachloroiodate; aldoximes;

D O I：

10.1016/S0040-4020(99)01047-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzyltrimethylammonium tetrachloroiodate (BTMA ICl4) acts as a convenient reagent to convert aldoximes to hydroximoyl chlorides by a simple procedure. When an aldoxime is treated with BTMA ICl4 in dichloromethane, the suspension of BTMA ICl4 shortly diasappears as the reaction proceeds. The resulting BTMA ICl2 can he precipitated out by adding diethyl ether. Not only stable aromatic and heteroaromatic hydroximoyl chlorides can be isolated by this method but also rather unstable aliphatic hydroximoyl chlorides can be generated in situ. 1,3-Dipole trapping with a dipolarophile is performed in one flask and in some cases the chlorination is successfully performed in the presence of dipolarophile and triethylamine. Effect of MS 4A has been examined. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1057 / 1064

页数：8

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