A convenient and useful method of preparation of α-bromo enones from the corresponding enones using organic ammonium tribromide (OATB)

被引：33

作者：

Bose, G ^{[1
]}

Barua, PMB ^{[1
]}

Chaudhuri, MK ^{[1
]}

Kalita, D ^{[1
]}

Khan, AT ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Guwahati 781039, Assam, India

来源：

CHEMISTRY LETTERS | 2001年 / 04期

关键词：

D O I：

10.1246/cl.2001.290

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Various acyclic a-bromo enones 2 as well as cyclic alpha -bromo enones 4 can be prepared from the corresponding acyclic enones 1 and cyclic enones 3 respectively, in a one-pot procedure by employing organic ammonium tribromide, such as cetyltrimethylammonium tribromide (CetTMATB) or tetrabutylammonium tribromide (TBATB) in presence of K2CO3 in dichloromethane at 0 degreesC to room temperature under very mild conditions in good yields(2).

引用

页码：290 / 291

页数：2

共 15 条

[1] Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions [J].

Arai, S ;

Nakayama, K ;

Ishida, T ;

Shioiri, T .

TETRAHEDRON LETTERS, 1999, 40 (22) :4215-4218

[2] An environmentally benign synthesis of organic ammonium tribromides (OATB) and bromination of selected organic substrates by tetrabutylammonium tribromide (TBATB) [J].

Chaudhuri, MK ;

Khan, AT ;

Patel, BK ;

Dey, D ;

Kharmawophlang, W ;

Lakshmiprabha, TR ;

Mandal, GC .

TETRAHEDRON LETTERS, 1998, 39 (44) :8163-8166

[3] SYNTHESIS OF PENTACYCLO[4.3.0.02,5.03,8.04,7]NONANE (HOMOCUBANE) AND SOME OF ITS DERIVATIVES [J].

DUNN, GL ;

DIPASQUO, VJ ;

HOOVER, JRE .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (04) :1454-+

[4]

GRIBBLE GW, 1996, PROGR CHEM ORGANIC N, P17

[5] Stereoselective synthesis of (2Z)-alpha-Bromo-alpha,beta-unsaturated esters via arsonium ylide [J].

Huang, ZZ ;

Wu, LL ;

Zhu, LS ;

Huang, X .

SYNTHETIC COMMUNICATIONS, 1996, 26 (04) :677-682

[6]

JANSSEN CGM, 1982, SYNTHESIS-STUTTGART, P389

[7] HALOGENATION AND OXIDATION WITH BENZYLTRIMETHYLAMMONIUM POLYHALIDES [J].

KAJIGAESHI, S ;

KAKINAMI, T .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1993, 51 (05) :366-376

[8]

KHAN AT, 2000, 13 INT C ORG SYNTH W

[9] ALPHA-KETO DIANION PRECURSORS VIA CONJUGATE ADDITIONS TO CYCLIC ALPHA-BROMO ENONES [J].

KOWALSKI, CJ ;

WEBER, AE ;

FIELDS, KW .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) :5088-5093

[10]

Larock R. C., 1999, COMPREHENSIVE ORGANI, P638

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