The 'Hirao reduction' revisited: a procedure for the synthesis of terminal vinyl bromides by the reduction of 1,1-dibromoalkenes

被引：68

作者：

Abbas, S ^{[1
]}

Hayes, CJ ^{[1
]}

Worden, S ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(00)00353-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient procedure for the synthesis of vinyl bromides is described, which involves the selective reduction of the corresponding 1,1-dibromoalkenes with dimethylphosphite and triethylamine. The 1,1-dibromoalkenes are obtained in excellent yields from the corresponding aldehydes via olefination with carbon tetrabromide and triphenylphosphine. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：3215 / 3219

页数：5

相关论文

共 11 条

[1]

Abbas S, 1999, SYNLETT, P1124

[2]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[3] Hypophosphite mediated carbon-carbon bond formation: a clean approach to radical methodology [J].

Graham, SR ;

Murphy, JA ;

Coates, D .

TETRAHEDRON LETTERS, 1999, 40 (12) :2415-2416

[4] REDUCTION OF GEM-DIBROMIDES WITH DIETHYL PHOSPHITE [J].

HIRAO, T ;

MASUNAGA, T ;

OHSHIRO, Y ;

AGAWA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (18) :3745-3747

[5] A CONVENIENT SYNTHESIS OF 1-BROMOOLEFINS AND ACETYLENES BY A CHAIN EXTENSION OF ALDEHYDES [J].

MATSUMOTO, M ;

KURODA, K .

TETRAHEDRON LETTERS, 1980, 21 (41) :4021-4024

[6] REACTION OF GEM-DIBROMOCYCLOPROPANES WITH POTASSIUM DIMETHYL PHOSPHITE IN LIQUID-AMMONIA - A HIGHLY STEREOSELECTIVE REDUCTION [J].

MEIJS, GF ;

DOYLE, IR .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3713-3716

[7] NEW SYNTHESIS OF 1,1-DIBROMOOLEFINS VIA PHOSPHINE-DIBROMOMETHYLENES - REACTION OF TRIPHENYLPHOSPHINE WITH CARBON TETRABROMIDE [J].

RAMIREZ, F ;

MCKELVIE, N ;

DESAI, NB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (09) :1745-&

[8] STEREOSELECTIVE SYNTHESIS OF NATURALLY-OCCURRING 7-(HETERO)ARYL-(2E,4E,6E)-2,4,6-HEPTATRIENAMIDES AND THEIR STRUCTURAL ANALOGS [J].

ROSSI, R ;

CARPITA, A ;

LIPPOLIS, V .

SYNTHETIC COMMUNICATIONS, 1991, 21 (03) :333-349

[9] SIMPLE AND SELECTIVE METHOD FOR RCHO-](E)-RCH=CHX CONVERSION BY MEANS OF A CHX3-CRCL2 SYSTEM [J].

TAKAI, K ;

NITTA, K ;

UTIMOTO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7408-7410

[10] A general and convenient synthetic method of geometrically pure (Z)-1-bromo-1-alkenes [J].

Uenishi, J ;

Kawahama, R ;

Shiga, Y ;

Yonemitsu, O ;

Tsuji, J .

TETRAHEDRON LETTERS, 1996, 37 (37) :6759-6762