ACTION OF TETRABUTYLAMMONIUM TRIBROMIDE WITH PARASUBSTITUTED CHALCONES IN PROTIC AND APROTIC MEDIA

被引：13
作者：
BERTHELOT, J
BENAMMAR, Y
DESMAZIERES, B
机构：
来源：
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1995年 / 73卷 / 09期
关键词：
BROMINATION; BROMOMETHOXYLATION; TETRABUTYLAMMONIUM TRIBROMIDE; (ALPHA-BETA) DIBROMODIHYDROCHALCONES; ALPHA-BROMO; BETA-METHOXYDIHYDROCHALCONES;
D O I：
10.1139/v95-189
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Bromination of the double bond of para-substituted chalcones under mild conditions in aprotic solvents is accomplished with high yields using tetrabutylammonium tribromide (TBABr(3)). In methanol, the main reaction is (alpha-beta) bromomethoxylation. Stereoselectivity, regioselectivity, and chemioselectivity of this bromomethoxylation reaction are described.
引用
收藏
页码：1526 / 1530
页数：5
相关论文
共 19 条
[1]   COMPARISON OF MOLECULAR BROMINE AND TRIBROMIDE ION AS BROMINATING REAGENTS .1. KINETIC EVIDENCE FOR DIFFERENT MECHANISMS OF ADDITION TO CYCLOHEXENE [J].
BELLUCCI, G ;
BIANCHINI, R ;
AMBROSETTI, R ;
INGROSSO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (18) :3313-3318
[2]   REGIOSELECTIVE BROMINATION IN AROMATIC SERIES .1. PARA-MONOBROMINATION OF PHENOLS AND AROMATIC-AMINES USING TETRABUTYLAMMONIUM TRIBROMIDE [J].
BERTHELOT, J ;
GUETTE, C ;
DESBENE, PL ;
BASSELIER, JJ ;
CHAQUIN, P ;
MASURE, D .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (12) :2061-2066
[3]  
DELAMARE PBD, 1982, ELECTROPHILIC ADDITI, P113
[4]   FLAVONE FORMATION IN THE WHEELER AURONE SYNTHESIS [J].
DONNELLY, JA ;
HIGGINBOTHAM, CL .
TETRAHEDRON, 1990, 46 (20) :7219-7226
[5]   CONSIDERATIONS ON THE EFFECT OF A CARBONYL GROUP ON THE RING-OPENING OF A NEIGHBORING BROMONIUM ION [J].
HEASLEY, VL ;
SPAITE, DW ;
SHELLHAMER, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2608-2611
[6]   REACTION OF HALOGENS WITH SOME ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES [J].
HEASLEY, VL ;
SHELLHAMER, DF ;
CARTER, TL ;
GIPE, DE ;
GIPE, RK ;
GREEN, RC ;
NORDEEN, J ;
REMPEL, TD ;
SPAITE, DW ;
HEASLEY, GE .
TETRAHEDRON LETTERS, 1981, 22 (26) :2467-2470
[7]   EFFECT OF N-BROMOSUCCINIMIDE (NBS) AND OTHER N-BROMINATING AGENTS ON THE BROMINATION OF ALPHA,BETA-UNSATURATED KETONES IN METHANOL [J].
HEASLEY, VL ;
LOUIE, TJ ;
LUTTRULL, DK ;
MILLAR, MD ;
MOORE, HB ;
NOGALES, DF ;
SAUERBREY, AM ;
SHEVEL, AB ;
SHIBUYA, TY ;
STANLEY, MS ;
SHELLHAMER, DF ;
HEASLEY, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2199-2204
[8]  
JOSHI MG, 1981, INDIAN J CHEM B, V20, P1090
[9]  
ORLOV VD, 1988, KHIM GETEROTSIKL, V3, P328
[10]  
RAGHAVAN RS, 1984, INDIAN J CHEM A, V23, P466
12