Selective mono-chlorination of aromatic compounds under mild conditions by tert-butyl hypochlorite in the presence of zeolites

被引:49
作者
Smith, K
Butters, M
Paget, WE
Goubet, D
Fromentin, E
Nay, B
机构
[1] Univ Wales Swansea, Dept Chem, Ctr Clean Chem, Swansea SA2 8PP, W Glam, Wales
[2] BP Res Ctr, New React Branch, Sunbury On Thames TW16 7LN, Middx, England
关键词
D O I
10.1039/a901395d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
tert-Butyl hypochlorite/HNa faujasite X in acetonitrile represents an efficient and highly regioselective system for mono-chlorination of a wide range of mono- and di-substituted aromatic substrates in mild conditions. Partially protonated faujasite X is far superior to amorphous silicas and to other zeolites in terms of efficiency and regioselectivity. Advantages of tert-butyl hypochlorite over other chlorinating reagents have been demonstrated. The method is suitable for large scale work.
引用
收藏
页码:83 / 90
页数:8
相关论文
共 41 条
[1]   ACIDIC DEGRADATION OF ZEOLITE CATALYSTS IN THE COURSE OF AROMATIC CHLORINATION USING SULFURYL CHLORIDE [J].
ANTENUCCI, D ;
DELAUDE, L ;
FRANSOLET, AM ;
LASZLO, P .
JOURNAL OF CATALYSIS, 1992, 135 (01) :92-98
[2]   Reactions of trialkyl phosphates, alkyl acetates, and tertiary butyl hypo- chlorite in the Friedel-Crafts syntheses [J].
Berman, N ;
Lowy, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :2596-2597
[3]   The reaction of alkylchloroamines with Grignard reagents [J].
Coleman, GH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 :3001-3005
[4]  
De la Mare P. B., 1976, ELECTROPHILIC HALOGE
[5]   VERSATILITY OF ZEOLITES AS CATALYSTS FOR RING OR SIDE-CHAIN AROMATIC CHLORINATIONS BY SULFURYL CHLORIDE [J].
DELAUDE, L ;
LASZLO, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5260-5269
[6]   HEIGHTENED SELECTIVITY IN AROMATIC NITRATIONS AND CHLORINATIONS BY THE USE OF SOLID SUPPORTS AND CATALYSTS [J].
DELAUDE, L ;
LASZLO, P ;
SMITH, K .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (12) :607-613
[7]  
Flanigen E.M., 1991, Introduction to zeolite science and practice, V2nd
[8]   ELECTROPHILIC CHLORINATION BY SULFURYL CHLORIDE IN PRESENCE OF SILICA-GEL [J].
HOJO, M ;
MASUDA, R .
SYNTHETIC COMMUNICATIONS, 1975, 5 (03) :169-171
[9]  
JIGAJINNI VB, 1981, J CHEM RES-S, P376
[10]  
LAROCK RC, 1989, COMPREHENSIVE ORGANI, P316