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

页码：83 / 95

页数：13

共 65 条

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