Convenient and stereoselective synthesis of (Z)-1-bromo-1-alkenes by microwave-induced reaction

被引：61

作者：

Kuang, CX ^{[1
]}

Senboku, H ^{[1
]}

Tokuda, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Sapporo, Hokkaido 0608628, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 23期

关键词：

(Z)-vinyl bromide; alpha; beta-unsaturated carboxylic acids decarboxylation; microwave irradiation;

D O I：

10.1016/S0040-4039(01)00595-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Z)-l-Bromo-l-alkenes were stereoselectively prepared in high yields in a short reaction time (0.2 1.0 min) by microwave irradiation of the corresponding 2,3-dibromoalkanoic acids in DMF in the presence of triethylamine. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3893 / 3896

页数：4

共 52 条

[1]

ABRAMOVITCH RA, 1991, ORG PREP PROCED INT, V23, P685

[2]

AHRA S, 1983, SYNTHESIS-STUTTGART, P1005

[3] FORMATION OF Z-1-VINYLIODIDES VIA THE WITTIG REACTION [J].

BESTMANN, HJ ;

RIPPEL, HC ;

DOSTALEK, R .

TETRAHEDRON LETTERS, 1989, 30 (39) :5261-5262

[4] SYNTHESIS OF 8Z,10Z-DODECADIENYL ACETATE USING A GENERAL-METHOD APPLICABLE TO Z,Z-1,3-DIENES [J].

BJORKLING, F ;

NORIN, T ;

UNELIUS, R .

SYNTHETIC COMMUNICATIONS, 1985, 15 (06) :463-472

[5]

BREVET JL, 1992, SYNTHESIS-STUTTGART, P1007

[6] VINYLIC ORGANOBORANES .13. A CONVENIENT STEREOSPECIFIC SYNTHESIS OF (Z)-1-HALO-1-ALKENES FROM 1-ALKYNES VIA (E)-1-ALKENYLBORANE DERIVATIVES WITH HALOGENS [J].

BROWN, HC ;

SUBRAHMANYAM, C ;

HAMAOKA, T ;

RAVINDRAN, N ;

BOWMAN, DH ;

MISUMI, S ;

UNNI, MK ;

SOMAYAJI, V ;

BHAT, NG .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6068-6075

[7] STEREOSPECIFIC CONVERSION OF ALKENYLBORONIC ACIDS INTO ALKENYL BROMIDES WITH INVERSION OF CONFIGURATION - STRIKING DIFFERENCES IN STEREOCHEMISTRY OF REPLACEMENT OF BORONIC ACID SUBSTITUENT BY BROMINE AND IODINE AND ITS SIGNIFICANCE IN TERMS OF REACTION-MECHANISM [J].

BROWN, HC ;

HAMAOKA, T ;

RAVINDRA.N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (19) :6456-6457

[8]

BROWN HC, 1986, SYNTHESIS-STUTTGART, P480

[9] A SIMPLE CONVERSION OF [E]- INTO THE ISOMERIC [Z]-2-(1-SUBSTITUTED-1-ALKENYL)-1,3,2-DIOXABORINANES, PROVIDING A CONVENIENT STEREOSPECIFIC SYNTHESIS OF BOTH [E]-1,2-DISUBSTITUTED AND [Z]-1,2-DISUBSTITUTED VINYL BROMIDES [J].

BROWN, HC ;

BHAT, NG .

TETRAHEDRON LETTERS, 1988, 29 (01) :21-24

[10] VINYLIC ORGANOBORANES .12. SYNTHESIS OF (Z)-1-HALO-1-ALKENES VIA HYDROBORATION OF 1-HALO-1-ALKYNES FOLLOWED BY PROTONOLYSIS [J].

BROWN, HC ;

BLUE, CD ;

NELSON, DJ ;

BHAT, NG .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6064-6067

← 1 2 3 4 5 6 →