LITHIUM CATION-CATALYZED WITTIG REACTIONS

被引:41
作者
HOOPER, DL [1 ]
GARAGAN, S [1 ]
KAYSER, MM [1 ]
机构
[1] UNIV NEW BRUNSWICK,DEPT CHEM,ST JOHN E2L 4L5,NB,CANADA
关键词
D O I
10.1021/jo00084a034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The condensation of stabilized phosphorane 1 with benzaldehyde is catalyzed by Li+ ion. In the presence of a large quantity of Li+, ylide 1 adds slowly to ketones with which it does not react under the usual reaction conditions. On the other hand, pretreatment of the ylide solution with trace amounts of BuLi tends to slow the reactions with aldehydes, probably by removing any traces of water and conjugate acid, the sources of protons that catalyzed these condensations.
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页码:1126 / 1128
页数:3
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