A CONVENIENT REAGENT FOR THE INTERMOLECULAR COUPLING OF ALDEHYDES AND KETONES TO FORM OLEFINS

被引:6
作者
CARROLL, AR
TAYLOR, WC
机构
[1] Department of Organic Chemistry, University of Sydney, NSW
关键词
D O I
10.1071/CH9901439
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
When aldehydes or ketones are treated with titanium tetrachloride and amalgamated magnesium turnings in tetrahydrofuran at 0° for 2 h and subsequently under reflux for 24 h, reductive coupling occurs to give olefin in high yield. The optimum ratio of carbonyl substrate to titanium reagent was found to be 1:4. Examples of symmetrical and mixed couplings are given. Intramolecular coupling was not successful. © 1990 ASEG.
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收藏
页码:1439 / 1443
页数:5
相关论文
共 7 条
[1]   NEW REAGENTS FOR INTERMOLECULAR AND INTRAMOLECULAR PINACOLIC COUPLING OF KETONES AND ALDEHYDES [J].
COREY, EJ ;
DANHEISER, RL ;
CHANDRASEKARAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :260-265
[2]   A SYNTHESIS OF (S,S)-(+)-GRAHAMIMYCIN-AL [J].
GHIRINGHELLI, D .
TETRAHEDRON LETTERS, 1983, 24 (03) :287-290
[3]  
LENOIR D, 1977, SYNTHESIS-STUTTGART, P553
[4]   THE APPLICATION OF LOW-VALENT TITANIUM REAGENTS IN ORGANIC-SYNTHESIS [J].
LENOIR, D .
SYNTHESIS-STUTTGART, 1989, (12) :883-897
[5]   TITANIUM-INDUCED REDUCTIVE COUPLING OF CARBONYLS TO OLEFINS [J].
MCMURRY, JE ;
FLEMING, MP ;
KEES, KL ;
KREPSKI, LR .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (17) :3255-3266
[6]   TITANIUM-INDUCED DICARBONYL-COUPLING REACTIONS [J].
MCMURRY, JE .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (11) :405-411
[7]  
MUKAIYAMA T, 1973, J CHEM LETT, P1041