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

被引:11
作者
Funabiki, K [1 ]
Ohtsuki, T [1 ]
Ishihara, T [1 ]
Yamanaka, H [1 ]
机构
[1] KYOTO INST TECHNOL, DEPT CHEM & MAT TECHNOL, SAKYO KU, KYOTO 606, JAPAN
关键词
D O I
10.1246/cl.1996.5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2,3,3-Trifluoro-1-tosyloxy-1-propenyllithium, generated from 2,3,3-trifluoro-1-propenyl p-toluenesulfonate with butyllithium, underwent coupling reaction with various carbonyl compounds to give good yields of 3,4,4-trifluoro-2-tosyloxy-2-butenyl alcohols, whose treatment with concentrated sulfuric acid at room temperature afforded the corresponding (Z)-alpha,beta-unsaturated difluoromethyl ketones in good yields.
引用
收藏
页码:5 / 6
页数:2
相关论文
共 18 条
[1]   PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES [J].
BEGUE, JP ;
BONNETDELPON, D .
TETRAHEDRON, 1991, 47 (20-21) :3207-3258
[2]   HOMOCHIRAL ALPHA-FLUOROKETONES FROM RACEMIC ALPHA-FLUOROCARBOXYLIC ESTERS AND ENANTIOMERICALLY PURE SULFOXIDES [J].
BRAVO, P ;
RESNATI, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (03) :218-219
[3]  
DEMAYO P, 1963, MOL REARRANGEMENTS, V1, P6
[4]   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
[5]   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
[6]  
HOJO M, 1986, SYNTHESIS-STUTTGART, P1013
[7]  
HOJO M, 1986, SYNTHESIS-STUTTGART, P1016
[8]  
Linderman R. J., 1993, Rev. Peetic. Toxicol., V2, P231
[9]   ADDITION OF ORGANOCUPRATES TO ACETYLENIC DIFLUOROMETHYL AND TRIFLUOROMETHYL KETONES - REGIOSPECIFIC SYNTHESIS OF BETA,BETA-DISUBSTITUTED UNSATURATED FLUORO KETONES [J].
LINDERMAN, RJ ;
LONIKAR, MS .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6013-6022
[10]   SYNTHESIS OF AND ANALYSIS OF THIOL ADDITIONS TO BETA-ALKYL-ALPHA,BETA-UNSATURATED TRIFLUOROMETHYL KETONES [J].
LINDERMAN, RJ ;
JAMOIS, EA ;
TENNYSON, SD .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) :957-962