Bromophilic substitution/carbophilic substitution cascade reactions of α,α-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles

被引：8
|
作者：
Tatar, Jovana [1 ]
Markovic, Rade [1 ,2 ]
Stojanovic, Milovan [1 ]
Baranac-Stojanovic, Marija [1 ,2 ]
机构：
[1] Ctr Chem ICTM, Belgrade 11000, Serbia
[2] Univ Belgrade, Fac Chem, Belgrade 11000, Serbia
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 37期
关键词：
alpha; alpha-Dibromomethylketone; Bromophilic reaction; Nucleophilic substitution; Cascade reactions; CATALYZED ASYMMETRIC HYDROGENATION; HALOPHILIC ATTACKS; KETONES; IODINE; PERHALOFLUOROALKANES; DEBROMINATION; MECHANISMS; DIBROMIDES; CHEMISTRY; LACTONES;
D O I：
10.1016/j.tetlet.2010.07.057
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
alpha,alpha-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford alpha-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained. (C) 2010 Elsevier Ltd. All rights reserved.
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收藏
页码：4851 / 4855
页数：5
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