SYNTHESIS OF ALPHA-SUBSTITUTED CYCLOHEXENONES BY THERMOLYSIS OF TERTIARY KETOSULFOXIDES

被引:4
作者
BARILLIER, D [1 ]
BENHIDA, R [1 ]
VAZEUX, M [1 ]
机构
[1] ISMRA UNIV,COMPOSES THIOORGAN LAB,CNRS,URA 480,6 BD MARECHAL JUIN,F-14032 CAEN,FRANCE
来源
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1993年 / 78卷 / 1-4期
关键词
ALPHA-FUNCTIONALIZED CYCLOHEXENONES; TERTIARY KETOSULFIDES AND KETOSULFOXIDES; SULFENYLATION AND DESHYDROSULFENYLATION; THERMOLYSIS;
D O I
10.1080/10426509308032425
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The sulfenylation-dehydrosulfenylation method, combined with carbon-carbon bond forming reactions, has been applied to the synthesis of some alpha-functionalized cyclohexenones 3. Hence, the sodium anion of the 2-methylthiocyclohexanone in THF reacts with primary, allyl and benzyl halides as well as with Michael acceptors to lead to the tertiary ketosulfides 1a-j. Further oxidation by NaIO4 and thermolysis in boiling toluene of the resulting sulfoxides 2 have been performed. The scope and limitations of this strategy are also discussed.
引用
收藏
页码:83 / 95
页数:13
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