ACYLATING FRIEDEL-CRAFTS COMPLEXES - MULTINUCLEAR NMR DATA AND CHEMICAL-REACTIVITY

被引:17
作者
BIGI, F [1 ]
CASNATI, G [1 ]
SARTORI, G [1 ]
PREDIERI, G [1 ]
机构
[1] UNIV PARMA,IST CHIM GEN & INORGAN,I-43100 PARMA,ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1991年 / 08期
关键词
D O I
10.1039/p29910001319
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-13, Al-27 and O-17 NMR investigations about the nature of the 1:1 system AlCl3.RCOCl (R = CH3, CH2Cl, CHCl2, CCl3) in CH2Cl2 show a donor-acceptor structure with the carbonyl oxygen involved in the metal co-ordination. The shift of the carbonyl group resonance (DELTA-delta) in C-13 and O-17 NMR spectra is strongly dependent on the electron-withdrawing power of the R group and shows a close connection with the reactivities of the different acyl complexes.
引用
收藏
页码:1319 / 1321
页数:3
相关论文
共 23 条
[1]  
AKHREM IS, 1985, DOKL AKAD NAUK SSSR+, V284, P627
[2]   UNUSUAL FRIEDEL-CRAFTS REACTIONS .8. SYNTHESIS OF 2-HYDROXYARYLGLYOXYLIC ACIDS VIA ORTHO-SPECIFIC OXALOYLATION OF PHENOLS WITH OXALYL CHLORIDE [J].
BIGI, F ;
CASIRAGHI, G ;
CASNATI, G ;
SARTORI, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (11) :2655-2657
[3]   UNUSUAL FRIEDEL-CRAFTS REACTIONS .9. ONE-STEP ORTHOACYLATION OF PHENOLS WITH ALPHA, BETA-UNSATURATED ACYL CHLORIDES - SYNTHESIS OF 2'-HYDROXYCHALCONES AND SORBICILLIN ANALOGS [J].
BIGI, F ;
CASIRAGHI, G ;
CASNATI, G ;
MARCHESI, S ;
SARTORI, G .
TETRAHEDRON, 1984, 40 (20) :4081-4084
[4]   DEPENDENCE OF ARYL ETHER ACYLATION UPON LEWIS ACID STOICHIOMETRY [J].
BUCKLEY, TF ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (09) :3056-3062
[5]   MECHANISM FOR C-ACYLATION - KINETIC STUDY ON ACETYLATION OF AROMATIC COMPOUNDS CATALYZED BY ALCL3 [J].
CORRIU, R ;
DORE, M ;
THOMASSI.R .
TETRAHEDRON, 1971, 27 (23) :5819-&
[6]   C-13 NUCLEAR MAGNETIC-RESONANCE STUDY ON THE NATURE OF RESONANCE INTERACTIONS IN 4-SUBSTITUTED BENZONITRILES, ACETOPHENONES, AND METHYL BENZOATES [J].
DELLERBA, C ;
SANCASSAN, F ;
NOVI, M ;
PETRILLO, G ;
MUGNOLI, A ;
SPINELLI, D ;
CONSIGLIO, G ;
GATTI, P .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3564-3568
[7]  
GERMAIN A, 1972, J CHEM SOC CHEM COMM, V8, P3177
[8]   THE SYSTEM ALUMINUM-CHLORIDE ACETYL-CHLORIDE IN SULFUR-DIOXIDE SOLVENT [J].
GLAVINCEVSKI, B ;
BROWNSTEIN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (06) :1005-1007
[9]   O-17-NMR SPECTROSCOPY AS A STRUCTURAL PROBE [J].
KLEMPERER, WG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (04) :246-254
[10]  
Le Carpentier J.-M, 1972, ACTA CRYSTALLOGR B, V28, P1421