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

共 44 条

[1] ETHYL PHENYLSULFINYL FLUOROACETATE, A NEW AND VERSATILE REAGENT FOR THE PREPARATION OF ALPHA-FLUORO-ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID ESTERS
ALLMENDINGER, T
[J]. TETRAHEDRON, 1991, 47 (27) : 4905 - 4914
[2] ALVERNHE G, 1994, B SOC CHIM FR, P167
[3] ANODIC FUNCTIONALIZATION OF VINYL SULFIDES - FORMAL ACCESS TO GEM OR VICINAL ARYL THIOETHER DICATIONS
ANDRES, DF
LAURENT, EG
MARQUET, BS
BENOTMANE, H
BENSADAT, A
[J]. TETRAHEDRON, 1995, 51 (09) : 2605 - 2618
[4] SYNTHETISCHE REAKTIONEN VON DIMETHYLFORMAMID .4. DARSTELLUNG VON BETA-CHLORVINYLALDEHYDEN AUS CARBONYLVERBINDUNGEN
ARNOLD, Z
ZEMLICKA, J
[J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1959, 24 (07) : 2385 - 2392
[5] SYNTHETIC REACTIONS OF DIMETHYLFORMAMIDE .2. THE REACTION OF KETALS WITH DIMETHYLFORMAMIDE AND PHOSGENE
ARNOLD, Z
ZEMLICKA, J
[J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1959, 24 (03) : 786 - 796
[6] VITAMIN-A ISOMERS .15. THE PREPARATION OF VICINAL DIFLUOROOLEFINIC CARBONYL-COMPOUNDS AND THEIR APPLICATION TO THE SYNTHESIS OF DIFLUOROETINAL ANALOGS
ASATO, AE
LIU, RSH
[J]. TETRAHEDRON LETTERS, 1986, 27 (29) : 3337 - 3340
[7] BLANCO L, 1985, B SOC CHIM FR, P455
[8] CLEMENCEAU D, 1993, TETRAHEDRON LETT, V43, P6903
[9] DEPUY CH, 1968, ACCOUNTS CHEM RES, V36, P1
[10] CONFORMATIONAL PREFERENCES OF ALPHA-FUNCTIONALIZED KETEN-S,N-ACETALS - POTENTIAL ROLE OF S..O AND S..S INTERACTIONS IN SOLUTION
DIXIT, AN
REDDY, KV
DESHMUKH, ARAS
RAJAPPA, S
GANGULY, B
CHANDRASEKHAR, J
[J]. TETRAHEDRON, 1995, 51 (05) : 1437 - 1448

← 1 2 3 4 5 →