Carbonylation reactions 8. Chlorocarbonylation reactions: catalytic formation of chloroacyl chlorides without phosgene and application to the synthesis of 2(H)-5-furanone

被引:9
作者
Bonnet, MC [1 ]
Carmona, N [1 ]
Tkatchenko, I [1 ]
机构
[1] CNRS, Chim Coordinat Lab, F-31077 Toulouse, France
关键词
chlorocarbonylation; chloroacyl chlorides; allyl halides; ethylene; palladium; reaction mechanisms;
D O I
10.1016/S1381-1169(98)00386-0
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Chloroacyl halides are obtained under mild conditions by catalytic carbonylation in halogenated solvents of allylic halides or ethylene and allyl chloride mixtures under pressure of CO and anhydrous HCl in the presence of PdCl2; excellent selectivities for dichloroacyl and chloroacyl derivatives are achieved. Allyl chloride is partly consumed for the regeneration of palladium chloride. The product of oxidative addition of HCl to the oligomeric [Pd(CO)Cl](n) formed in situ by reaction of CO on PdCl2 is proposed as the first step towards the generation of the active species. (C) 1999 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:181 / 195
页数:15
相关论文
共 47 条
[1]  
Alderson T., 1962, US patent, Patent No. [3,065,242, 3065242]
[2]   CHLOROCARBONYLATION OF UNSATURATED SUBSTRATES CATALYZED BY PALLADIUM COMPLEXES IN THE PRESENCE OF ANHYDROUS HCL [J].
BENARD, N ;
BONNET, MC ;
LECOLIER, S ;
TKATCHENKO, I .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (18) :1448-1450
[3]   A ROUTE TO PROSTAGLANDIN PRECURSORS FROM 1-(PHENYLTHIO)-2-OCTENYLLITHIUM [J].
BINNS, MR ;
HAYNES, RK ;
LAMBERT, DE ;
SCHOBER, PA .
TETRAHEDRON LETTERS, 1985, 26 (28) :3385-3388
[4]  
Bonnet Marie-Laure, UNPUB
[5]   CARBONYLATION OF ORGANIC ALLYL MOIETIES .3. THE CASE OF METHOXYOCTADIENES AND THE ROLE OF H+HALIDE-, R4N+BF4- COCATALYSTS [J].
BONNET, MC ;
COOMBES, J ;
MANZANO, B ;
NEIBECKER, D ;
TKATCHENKO, I .
JOURNAL OF MOLECULAR CATALYSIS, 1989, 52 (02) :263-276
[6]  
BRIMA TS, 1982, Patent No. 4356310
[7]  
CHERDON H, 1966, Patent No. 1228065
[8]   CATALYSIS OF OLEFIN AND CARBON-MONOXIDE INSERTION REACTIONS [J].
CHIUSOLI, GP .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (12) :422-427
[9]  
COULSON D, 1972, INORG SYNTH, V13, P112
[10]  
DELLAMICO DB, 1984, INORG CHEM, V23, P137