THE C-ARYLATION OF ALPHA-CYANO ESTERS AND MALONONITRILES BY ARYLLEAD(IV) TRIACETATES

被引:13
作者
KOZYROD, RP
MORGAN, J
PINHEY, JT
机构
[1] Department of Organic Chemistry, University of Sydney
关键词
D O I
10.1071/CH9910369
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The arylation of soft carbon nucleophiles by aryllead(IV) triacetates has been extended to alpha-cyano esters and malononitriles. Arylation did not occur with the parent compounds, ethyl cyanoacetate and malononitrile, but in both series monosubstituted compounds reacted to give alpha-aryl derivatives in synthetically useful yields. A study of the effect of some tertiary aromatic amines and dimethyl sulfoxide, substances which complex with lead(IV), has been carried out, and in two cases the influence of bulky alpha-substituents has been examined.
引用
收藏
页码:369 / 376
页数:8
相关论文
共 19 条
[1]  
ABROMOVITCH RA, 1988, TETRAHEDRON, V44, P3039
[2]   THE CHEMISTRY OF ARYL-LEAD(IV) TRICARBOXYLATES - REACTION WITH VINYLOGOUS BETA-KETO-ESTERS [J].
ACKLAND, DJ ;
PINHEY, JT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2689-2694
[3]   PENTAVALENT ORGANOBISMUTH REAGENTS .3. PHENYLATION OF ENOLS AND OF ENOLATE AND OTHER ANIONS [J].
BARTON, DHR ;
BLAZEJEWSKI, JC ;
CHARPIOT, B ;
FINET, JP ;
MOTHERWELL, WB ;
PAPOULA, MTB ;
STANFORTH, SP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2667-2675
[4]   PENTAVALENT ORGANOBISMUTH REAGENTS .2. THE PHENYLATION OF PHENOLS [J].
BARTON, DHR ;
BHATNAGAR, NY ;
BLAZEJEWSKI, JC ;
CHARPIOT, B ;
FINET, JP ;
LESTER, DJ ;
MOTHERWELL, WB ;
PAPOULA, MTB ;
STANFORTH, SP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2657-2665
[5]   PENTAVALENT ORGANOBISMUTH REAGENTS .6. COMPARATIVE MIGRATORY APTITUDES OF ARYL GROUPS IN THE ARYLATION OF PHENOLS AND ENOLS BY PENTAVALENT BISMUTH REAGENTS [J].
BARTON, DHR ;
BHATNAGAR, NY ;
FINET, JP ;
MOTHERWELL, WB .
TETRAHEDRON, 1986, 42 (12) :3111-3122
[6]   THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .7. THE POSSIBLE ROLE OF RADICAL MECHANISMS IN THE PHENYLATION PROCESS FOR BISMUTH(V), AND RELATED LEAD(IV), IODINE(III), AND ANTIMONY(V) REAGENTS [J].
BARTON, DHR ;
FINET, JP ;
GIANNOTTI, C ;
HALLEY, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :241-249
[7]  
BISCHOFF CA, 1895, CHEM BER, V28, P2616
[8]   OXIDATIVE CARBON-CARBON COUPLING .1. OXIDATIVE COUPLING OF ALPHA-SUBSTITUTED BENZYL CYANIDES [J].
DEJONGH, HAP ;
DEJONGE, CRH ;
MIJS, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (21) :3160-&
[9]   THE CHEMISTRY OF ARYLLEAD TRICARBOXYLATES - SYNTHESIS OF SOME ALPHA-ARYL ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
KOPINSKI, RP ;
PINHEY, JT .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1983, 36 (02) :311-316
[10]   THE CHEMISTRY OF ARYLLEAD(IV) TRICARBOXYLATES - REACTION WITH DERIVATIVES OF MALONIC-ACID - NEW ROUTES TO ALPHA-ARYL CARBOXYLIC-ACIDS AND ARYLATED BARBITURIC-ACID DERIVATIVES [J].
KOPINSKI, RP ;
PINHEY, JT ;
ROWE, BA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (06) :1245-1254