THE REGIOSELECTIVE CLEAVAGE OF ARYL TOSYLATES BY ELECTROCHEMICAL REDUCTION

被引:26
作者
CIVITELLO, ER [1 ]
RAPOPORT, H [1 ]
机构
[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720
关键词
D O I
10.1021/jo00029a010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The electrochemical reductions of eight bis(tosyloxy)benzanoid compounds were studied as a method for the regioselective cleavage of aryl tosylates. For the methyl bis(tosyloxy)benzoate isomers, a strong preference was observed for cleavage of the tosyl group in conjugation with the electron-withdrawing ester moiety. Thus it was possible to selectively cleave tosyl groups to the ortho or para positions over tosyl groups at the meta positions. The bis(tosyloxy)anisole isomers displayed the opposite regioselectivity favoring cleavage of tosyl groups that were meta to the electron-donating methoxy substituent. The general electrochemical process for the reduction of aryl tosylates has been shown to be selective, high yielding, and reproducible on gram quantities.
引用
收藏
页码:834 / 840
页数:7
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