The ring-opening reaction of 3,3,3-trifluoropropene oxide with carbanions: Reaction of alpha-cyanocarbanions

被引:13
作者
Katagiri, T [1 ]
Akizuki, M [1 ]
Kuriyama, T [1 ]
Shinke, S [1 ]
Uneyama, K [1 ]
机构
[1] OKAYAMA UNIV, FAC ENGN, DEPT APPL CHEM, OKAYAMA 700, JAPAN
关键词
D O I
10.1246/cl.1997.549
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nucleophilic ring-opening reaction of 3,3,3-trifluoropropene oxide (TFPO) was studied. Reaction of TFPO with carbanions stabilized by cyano group gave gamma-cyanohydrins in moderate to good yields. Meanwhile, reaction of the carbanions from malonic ester and nitromethane resulted in recovery of TFPO.
引用
收藏
页码:549 / 550
页数:2
相关论文
共 13 条
[1]  
[Anonymous], 1991, Fluorine in Bioorganic Chemistry
[2]  
FURUASHI K, 1992, CHIRALITY IND
[3]  
Hudlicky M., 1995, CHEM ORGANIC FLUORIN, V1st
[4]  
KHARASCH MS, 1954, GRIGNARD REACTION NO, pCH14
[5]  
KUHKAR VP, 1995, FLUORINE CONTAINING
[6]   THE RING-CLEAVAGE REACTIONS OF 1,1,1-TRIFLUORO-2,3-EPOXYPROPANE [J].
MCBEE, ET ;
HATHAWAY, CE ;
ROBERTS, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (15) :3851-3854
[7]   THE PREPARATION AND PROPERTIES OF 3,3,3-TRIFLUORO-1,2-EPOXYPROPANE [J].
MCBEE, ET ;
BURTON, TM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (12) :3022-3023
[8]   CHIRAL SYNTHESIS VIA ORGANOBORANES .40. SELECTIVE REDUCTIONS .55. A SIMPLE ONE-POT SYNTHESIS OF THE ENANTIOMERS OF (TRIFLUOROMETHYL)OXIRANE - A GENERAL-SYNTHESIS IN HIGH OPTICAL PURITIES OF ALPHA-TRIFLUOROMETHYL SECONDARY ALCOHOLS VIA THE RING-CLEAVAGE REACTIONS OF THE EPOXIDE [J].
RAMACHANDRAN, PV ;
GONG, BQ ;
BROWN, HC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01) :41-46
[9]  
SAEKI N, 1990, IUMS C BACT MYC OS J
[10]   Highly stereocontrolled access to 1,1,1-trifluoro-2,3-epoxypropane via lipase-mediated kinetic resolution of 1,1,1-trifluoro-3-(phenylthio)propan-2-ol and its application [J].
Shimizu, M ;
Sugiyama, K ;
Fujisawa, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (09) :2655-2659