OXIDATION OF ACETYLENES WITH TERT-BUTYL HYDROPEROXIDE CATALYZED BY SELENIUM DIOXIDE - ALPHA,ALPHA'-DIOXYGENATION OF INTERNAL ALKYNES

被引:44
作者
CHABAUD, B [1 ]
SHARPLESS, KB [1 ]
机构
[1] STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
关键词
D O I
10.1021/jo01337a045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unlike olefins, acetylenes show a strong tendency to undergo α, α&-dioxygenation upon reaction with Se02. The oxidation of ten different acetylenes allowed assignment of the reactivity sequence: CH2≃CH > CH3. Alkynes bearing one methylene and one methine substituent afforded the enynone as the major product. © 1979, American Chemical Society. All rights reserved.
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页码:4202 / 4204
页数:3
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