Sodium hydroxide-promoted reaction of 1-substituted 2,3,3-trifluoro-prop-1-enyl toluene-p-sulfonates with alcohols. First efficient and convenient access to alpha-fluoro-beta,beta-dialkoxy ketones

被引：12

作者：

Funabiki, K

Suzuki, C

Takamoto, S

Matsui, M

Shibata, K

机构：

[1] Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 18期

关键词：

D O I：

10.1039/a705495e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,3,3-Triffuoro-1-aryl- or -1-alkyl-prop-1-enyl toluene-p-sulfonates 1, readily available from 2,2,3,3-tetrafluoropropanol, react smoothly with alcohols in the presence of sodium hydroxide at ambient temperature for 1 h to afford the corresponding alpha-fluoro-beta,beta-dialkoxy ketones 2 in good to excellent yields.

引用

收藏

页码：2679 / 2680

页数：2

相关论文

共 33 条

[1] ENZYME-INHIBITORS - GROUND-STATE TRANSITION-STATE ANALOGS [J].

ABELES, RH .

DRUG DEVELOPMENT RESEARCH, 1987, 10 (04) :221-234

[2] Reaction of thioglycolate with alpha-fluoro-beta-(phenylthio)enones (or -enals): Synthesis of substituted alpha-carboxy-gamma-fluorothiophenes [J].

Andres, DF ;

Laurent, EG ;

Marquet, BS .

TETRAHEDRON LETTERS, 1997, 38 (06) :1049-1052

[3] EFFICIENT ELECTROPHILIC FLUORINATION OF BETA-DICARBONYL COMPOUNDS WITH THE SELECTFLUOR REAGENT F-TEDA-BF4 (1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE)) [J].

BANKS, RE ;

LAWRENCE, NJ ;

POPPLEWELL, AL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :343-344

[4] SELECTIVITY IN THE SYNTHESIS OF FLUORINATED HETEROCYCLES FROM ALPHA,BETA-UNSATURATED PERFLUOROACYL DERIVATIVES (OR THEIR SYNTHETIC EQUIVALENTS) AND 1,2-BIS-NUCLEOPHILES [J].

DONDY, B ;

DOUSSOT, P ;

IZNADEN, M ;

MUZARD, M ;

PORTELLA, C .

TETRAHEDRON LETTERS, 1994, 35 (25) :4357-4360

[5] ELECTROLYTIC REACTIONS OF FLUORO ORGANIC-COMPOUNDS .7. ANODIC METHOXYLATION AND ACETOXYLATION OF 2,2,2-TRIFLUOROETHYL SULFIDES - PREPARATION OF HIGHLY USEFUL TRIFLUOROMETHYLATED BUILDING-BLOCKS [J].

FUCHIGAMI, T ;

YAMAMOTO, K ;

NAKAGAWA, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :137-142

[6]

FUCHIGAMI T, 1987, J ORG CHEM, V87, P5489

[7] FLUORIDE ION-PROMOTED REACTION OF POLYFLUORO-1-PROPENYL P-TOLUENESULFONATE WITH AMINES - HIGHLY EFFICIENT AND GENERAL ACCESS TO (Z)-ALPHA-FLUORO-BETA-AMINO ACRYLALDEHYDES [J].

FUNABIKI, K ;

OHTSUKI, T ;

ISHIHARA, T ;

YAMANAKA, H .

CHEMISTRY LETTERS, 1994, (06) :1075-1078

[8] Efficient and convenient route to (Z)-alpha,beta-unsaturated difluoromethyl ketones based on the reaction of 2,3,3-trifluoro-1-tosyloxy-1-propenyllithium with carbonyl compounds [J].

Funabiki, K ;

Ohtsuki, T ;

Ishihara, T ;

Yamanaka, H .

CHEMISTRY LETTERS, 1996, (01) :5-6

[9] REACTIONS OF 1-SUBSTITUTED-POLYFLUORO-1-PROPENYL P-TOLUENESULFONATES WITH BIFUNCTIONAL NITROGEN NUCLEOPHILES - A NEW EXPEDIENT ACCESS TO MONOFLUORINATED NITROGEN-HETEROCYCLES [J].

FUNABIKI, K ;

OHTSUKI, T ;

ISHIHARA, T ;

YAMANAKA, H .

CHEMISTRY LETTERS, 1995, (03) :239-240

[10] An efficient and general entry to (Z)-alpha-fluoro-beta-substituted acrylaldehydes based on the coupling reaction of alpha-fluoro-beta-amino acrylaldehydes with organolithium reagents [J].

Funabiki, K ;

Kurita, T ;

Matsui, M ;

Shibata, K .

CHEMISTRY LETTERS, 1997, (08) :739-740

← 1 2 3 4 →