ELECTROREDUCTIVE RING-OPENING OF ALPHA,BETA-EPOXY CARBONYL-COMPOUNDS AND THEIR HOMOLOGS THROUGH RECYCLABLE USE OF DIPHENYL DISELENIDE OR DIPHENYL DITELLURIDE AS A MEDIATOR

被引:47
作者
INOKUCHI, T [1 ]
KUSUMOTO, M [1 ]
TORII, S [1 ]
机构
[1] OKAYAMA UNIV,FAC ENGN,DEPT APPL CHEM,OKAYAMA 700,JAPAN
关键词
D O I
10.1021/jo00292a032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel access to β-hydroxy carbonyl compounds from the corresponding a,0-epoxy carbonyl compounds has been attained through the recyclable use of diphenyl diselenide or diphenyl ditelluride as an electroreduction mediator in a MeOH-NaC1O4-(Pt) system. α,β-Epoxy ketones are converted to the corresponding aldols in the presence of malonic esters. Similarly, a,0-epoxy esters and nitriles can be reduced to the corresponding β-hydroxy compounds in the presence of acetic acid. © 1990, American Chemical Society. All rights reserved.
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页码:1548 / 1553
页数:6
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