REACTION OF ALPHA-TRIFLUOROMETHYLACRYLIC ACID WITH VARIOUS UNSATURATED GRIGNARD-REAGENTS

被引:27
作者
WATANABE, S [1 ]
SUGAHARA, K [1 ]
FUJITA, T [1 ]
SAKAMOTO, M [1 ]
KITAZUME, T [1 ]
机构
[1] TOKYO INST TECHNOL,DEPT BIOENGN,MIDORI KU,YOKOHAMA,KANAGAWA 227,JAPAN
关键词
D O I
10.1016/S0022-1139(00)80094-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reactions of 2-(trifluoromethyl)propenoic acid (I) with unsaturated Grignard reagents have been examined. Vinylmagnesium bromide with I gave 2-difluoromethylene-4-pentenoic acid (II) and analogous acids were obtained from propenyl and butenyl magnesium halides. The iodolactonization of II gave 2-difluoromethylene-4-iodomethyl-gamma-lactone (III). 2-Monofluoromethylene-4-penten-1-ol (IV) was obtained by the reduction of II with lithium aluminium hydride.
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页码:201 / 206
页数:6
相关论文
共 5 条
[1]   STEREOSELECTIVE EPOXIDATION OF ACYCLIC OLEFINIC CARBOXYLIC-ACIDS VIA IODO-LACTONIZATION [J].
BARTLETT, PA ;
MYERSON, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (12) :3950-3952
[2]   FACILE SYNTHESES OF FLUORINE-CONTAINING ALPHA, BETA-UNSATURATED ACIDS AND ESTERS FROM 2-TRIFLUOROMETHYLACRYLIC ACID [J].
FUCHIKAMI, T ;
SHIBATA, Y ;
SUZUKI, Y .
TETRAHEDRON LETTERS, 1986, 27 (27) :3173-3176
[3]  
KITAZUME T, 1988, SYNTHESIS-STUTTGART, P614
[4]   ULTRASOUND-PROMOTED SYNTHESIS OF ALPHA-DIFLUOROMETHYLATED CARBOXYLIC-ACIDS [J].
KITAZUME, T ;
OHNOGI, T ;
MIYAUCHI, H ;
YAMAZAKI, T ;
WATANABE, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23) :5630-5632
[5]   ESTER ENOLATE CLAISEN REARRANGEMENTS OF ALLYL ALPHA-FLUOROACETATES AND ALPHA-FLUOROPROPANOATES [J].
WELCH, JT ;
PLUMMER, JS ;
CHOU, TS .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :353-359