Zinc Barbier reaction of propargyl halides in water

被引:48
作者
Bieber, LW [1 ]
da Silva, MF [1 ]
da Costa, RC [1 ]
Silva, LOS [1 ]
机构
[1] Univ Fed Pernambuco, Dept Quim Fundamental, BR-50670901 Recife, PE, Brazil
关键词
D O I
10.1016/S0040-4039(98)00641-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of propargyl halides and carbonyl compounds with zinc powder proceeds in concentrated aqueous salt solutions affording with high selectivity homopropargylic alcohols. Preparatively useful yields are obtained with aromatic and aliphatic aldehydes. Ketones and 2-hydroxybenzaldehydes react partially. A surface process of two SET is discussed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3655 / 3658
页数:4
相关论文
共 19 条
[1]  
Barbier P., 1899, CR HEBD ACAD SCI, V128, P110
[2]   Reformatsky reaction in water: Evidence for a radical chain process [J].
Bieber, LW ;
Malvestiti, I ;
Storch, EC .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9061-9064
[3]  
Blomberg C., 1993, The Barbier reaction and related one-step processes
[4]   ALLYLSTANNATION .6. ALLYLATION AND ALLENYLATION OF ALDEHYDES AND KETONES BY ALLYL-TIN AND ALLENYL-TIN CHLORIDES IN THE PRESENCE OF WATER [J].
BOARETTO, A ;
MARTON, D ;
TAGLIAVINI, G ;
GAMBARO, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 286 (01) :9-16
[5]   1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS [J].
CHAN, TH ;
LI, CJ ;
LEE, MC ;
WEI, ZY .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05) :1181-1192
[6]   CROSSED ALDOL TYPE CONDENSATION-REACTIONS IN AQUEOUS-MEDIA [J].
CHAN, TH ;
LI, CJ ;
WEI, ZY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) :505-507
[7]  
Frankland E, 1849, ANN CHEM PHARM, V71, P213
[8]  
FREUND A, 1861, LIEBIGS ANN CHEM, V118, P1
[9]  
Grignard V, 1900, CR HEBD ACAD SCI, V130, P1322
[10]   RESEARCHES ON ACETYLENIC COMPOUNDS .21. REFORMATSKY REACTIONS WITH PROPARGYL BROMIDES [J].
HENBEST, HB ;
JONES, ERH ;
WALLS, IMS .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (OCT) :2696-2700