HALOGENATED KETENES .32. CYCLO-ADDITION OF DICHLOROKETENE WITH SILYL ENOL ETHERS

被引:26
作者
BRADY, WT
LLOYD, RM
机构
[1] Department of Chemistry, North Texas State University, Denton
关键词
D O I
10.1021/jo01328a048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The generation of dichloroketene by the zinc dechlorination of trichloroacetyl chloride in the presence of silyl enol ethers results in good yields of 2, 2-dichloro-3-siloxycyclobutanones. The silyl substituent is easily removed to yield the 3-hydroxycyclobutanones. Several of the siloxycyclobutanones and 3-hydroxycyclobutanones were thermally unstable and underwent a silicon migration and ring-opening reaction to yield l, l-dichloro-2, 4-diones. This thermal instability is related to conformational effects in the cyclobutanone ring. The chlorine atoms on the 2, 2-dichloro-3-siloxycyclobutanones are readily removed by tri-n-butyltin hydride reduction. © 1979, American Chemical Society. All rights reserved.
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页码:2560 / 2564
页数:5
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