SELECTIVE ACTIVATION OF PRIMARY CARBOXYLIC-ACIDS BY ELECTRON-RICH TRIARYLBISMUTHANES - APPLICATION TO AMIDE AND ESTER SYNTHESIS UNDER NEUTRAL CONDITIONS

被引:22
作者
OGAWA, T [1 ]
HIKASA, T [1 ]
IKEGAMI, T [1 ]
ONO, N [1 ]
SUZUKI, H [1 ]
机构
[1] EHIME UNIV,FAC SCI,DEPT CHEM,MATSUYAMA,EHIME 790,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 23期
关键词
D O I
10.1039/p19940003473
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
On being heated in benzene in the presence of tris(methoxyphenyl) bismuthanes 1b-1e, primary carboxylic acids are selectively activated to couple with amines and alcohols to produce the corresponding amides and esters in satisfactoy yields, while secondary, tertiary and aromatic carboxylic acids remain unaffected. 2-Benzylmalonic acid is similarly converted into its corresponding diamides and diesters, but 2,2-dibenzylmalonic acid suffers extensive decarboxylation and, in the presence of aromatic olefins, it undergoes a novel [3 + 2]-type cycloaddition reaction to form 4-substituted 2,2-dibenzyl-4-butanolides in low to fair yields.
引用
收藏
页码:3473 / 3478
页数:6
相关论文
共 27 条