Anodic fluorination of vinyl sulfides-synthesis of alpha-fluoro-beta-thio-alpha,beta-unsaturated carbonyl compounds

被引：32

作者：

Andres, DF ^{[1
]}

Dietrich, U ^{[1
]}

Laurent, EG ^{[1
]}

Marquet, BS ^{[1
]}

机构：

[1] UNIV LYON 1,CNRS,UMR 56222,LAB CHIM ORGAN 3,F-69622 VILLEURBANNE,FRANCE

来源：

TETRAHEDRON | 1997年 / 53卷 / 02期

关键词：

anodic oxidation; electrofluorination; vinyl sulfides; enol thioethers; fluoro vinyl sulfides; alpha-fluoro enals; alpha-fluoro enones; alpha-fluoro alkenoates; dehydrofluorination;

D O I：

10.1016/S0040-4020(96)00997-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of new title compounds 3 was synthesised in moderate to excellent yield, by anodic fluorination of their corresponding hydrogenated homologues 1 in Et(3)N,3HF/CH3CN, followed by a chemical dehydrofluorination step. From vinyl sulfides, we showed that anodically generated vicinal difluoro adducts 2 were easily dehydrofluorinated by an E1cB mechanism, leading to 3 with high stereoselectivity in most cases. In contrast, the anodic behaviour of a thio flavone in the same media was slightly different, giving rise to the formation of vinylic fluoride 3 during the anodic fluorination. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：647 / 658

页数：12

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