Solvent incorporation in bromination of alkynes with tetrabutylammonium tribromide in methanol

被引：12

作者：

Berthelot, J

Benammar, Y

Desmazieres, B

机构：

[1] Lab. de Chimie Organique Structurale, UMR 172, Université P. et M. Curie, 75252 Paris, Cedex 05, 4, Place Jussieu

来源：

SYNTHETIC COMMUNICATIONS | 1997年 / 27卷 / 16期

关键词：

D O I：

10.1080/00397919708004163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of tetrabutylammonium tribromide (TBABr(3)) with mono and disubstituted alkynes in methanol at 20 degrees C leads to the formation of mainly the corresponding alpha,alpha-dibromo, beta,beta-dimethoxyalkane and the E-(alpha,beta)-dibromoalkene. The additions are faster using sonication.

引用

页码：2865 / 2876

页数：12

共 18 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]

BENAMMAR Y, 1994, THESIS U PARIS 6 PAR

[3] A MILD AND EFFICIENT SONOCHEMICAL BROMINATION OF ALKENES USING TETRABUTYLAMMONIUM TRIBROMIDE [J].

BERTHELOT, J ;

BENAMMAR, Y ;

LANGE, C .

TETRAHEDRON LETTERS, 1991, 32 (33) :4135-4136

[4] FACILE FORMATIONS OF KETALS OF ALPHA,ALPHA-DIHALOACETOPHENONES [J].

BOVONSOMBAT, P ;

MCNELIS, E .

TETRAHEDRON LETTERS, 1992, 33 (29) :4123-4126

[5] CUPRIC HALIDE HALOGENATIONS [J].

CASTRO, CE ;

GAUGHAN, EJ ;

OWSLEY, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (02) :587-&

[6]

DELAMARE PBD, 1982, ELECTROPHILIC ADDITI, pCH3

[7]

DELAMARE PBD, 1982, ELECTROPHILIC ADDITI, pCH7

[8] KINETICS OF HALOGENATION OF OLEFINS AND ACETYLENES .6. BROMINATION OF TRANS-CINNAMIC ACID AND ITS METHYL-ESTER [J].

DEYOUNG, S ;

BERLINER, E .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (07) :1088-1092

[9]

FICINI J, 1953, CR ACAD SCI C CHIM, V267, P731

[10]

GRIESBAUM K, 1972, CHEM BER, V105, P3838

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