The synthesis of alpha-monofluorovinylphosphonates by a Peterson type olefination reaction

被引:15
作者
Keeney, A [1 ]
Nieschalk, J [1 ]
OHagan, D [1 ]
机构
[1] DEPT CHEM,SCI LABS,DURHAM DH1 3LE,ENGLAND
关键词
synthesis; alpha-monofluorovinylphosphonates; Peterson olefination; F-19-; H-1 and P-31-NMR spectroscopy;
D O I
10.1016/S0022-1139(96)03460-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reaction of alpha-lithium-alpha-fluoro-alpha-trimethylsilyl-methylphosphonate 2 with aldehydes 3a-fleads to alpha-fluorovinylphosphonates 4a-fby a Peterson type olefination reaction.
引用
收藏
页码:59 / 62
页数:4
相关论文
共 18 条
[1]   SYNTHESIS OF ALPHA-FLUOROVINYLPHOSPHONATES [J].
BLACKBURN, GM ;
PARRATT, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1417-1424
[2]  
BLACKBURN GM, 1981, CHEM IND-LONDON, P134
[3]   THE SYNTHESIS OF ALPHA-FLUOROALKYLPHOSPHONATES [J].
BLACKBURN, GM ;
PARRATT, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1425-1430
[4]  
BLACKBURN GM, 1986, CHEM SCRIPTA, V26, P21
[5]   PREPARATION OF DIFLUOROPHOSPHONOACETIC ACID AND ITS DERIVATIVES [J].
BURTON, DJ ;
SPRAGUE, LG .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1523-1527
[6]   MICHAELIS-ARBUZOV PREPARATION OF HALO-F-METHYLPHOSPHONATES [J].
BURTON, DJ ;
FLYNN, RM .
JOURNAL OF FLUORINE CHEMISTRY, 1977, 10 (04) :329-332
[7]   PREPARATION, STABILITY, REACTIVITY AND SYNTHETIC UTILITY OF A CADMIUM STABILIZED COMPLEX OF DIFLUOROMETHYLENE PHOSPHONIC ACID ESTER [J].
BURTON, DJ ;
TAKEI, R ;
SHINYA, S .
JOURNAL OF FLUORINE CHEMISTRY, 1981, 18 (02) :197-202
[8]   ALLYLATIONS OF [(DIETHOXYPHOSPHINYL)DIFLUOROMETHYL]ZINC BROMIDE AS A CONVENIENT ROUTE TO 1,1-DIFLUORO-3-ALKENEPHOSPHONATES [J].
BURTON, DJ ;
SPRAGUE, LG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :613-617
[9]  
CARY FA, 1972, J ORG CHEM, V37, P939
[10]   MONOFLUOROPHOSPHONATES AS PHOSPHATE MIMICS IN BIOORGANIC CHEMISTRY - A COMPARATIVE-STUDY OF CH2-PHOSPHONATE, CHF-PHOSPHONATE AND CF2-PHOSPHONATE ANALOGS OF SN-GLYCEROL-3-PHOSPHATE AS SUBSTRATES FOR SN-GLYCEROL-3-PHOSPHATE DEHYDROGENASE [J].
NIESCHALK, J ;
OHAGAN, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (07) :719-720