ELECTROPHILIC SUBSITUTION IN 2,1-BENZISOTHIAZOLES

被引:16
作者
DAVIS, M
WHITE, AW
机构
[1] Department of Chemistry, La Trobe University, Bundoora
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 16期
关键词
D O I
10.1039/j39690002189
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bromination of 2,1-benzisothiazole (I) under conditions in which Br + is the electrophilic species gives a mixture of 5- and 7-bromo-2,1-benzisothiazole, together with a smaller quantity of 4,7-dibromo-2,1-benzisothiazole. Nitration of 2,1-benzisothiazole affords mainly 5-nitro-2,1-benzisothiazole with smaller quantities of the 7-nitro-and 4-nitro-isomers. Nitration of monosubstituted 2,1-benzisothiazoles gives products which indicate that the substituent group already present in the benzenoid ring is the decisive directing influence.
引用
收藏
页码:2189 / &
相关论文
共 13 条
[1]  
Altaf-ur-Rahman, 1966, TETRAHEDRON S7, P49
[2]   Several experiments on anthranil and methyl-anthranil. [J].
Bamberger, E ;
Lublin, J .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1909, 42 :1676-1707
[3]  
DAVIS M, 1968, CHEM COMMUN, P1547
[4]  
DAVIS M, IN PRESS
[5]  
DAVIS M, UNPUBLISHED WORK
[6]   THE 5-BROMINATION AND 8-BROMINATION OF QUINOLINE AND SOME OF ITS DERIVATIVES [J].
DELAMARE, PBD ;
KIAMUDDIN, M ;
RIDD, JH .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (FEB) :561-565
[7]   SYNTHESE VON ISOTHIONAPHTHEN .1. [J].
MAYER, R ;
RICHTER, S ;
KLEINERT, H ;
GEWALD, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1962, 74 (03) :118-&
[8]  
PALMER MH, 1967, HETEROCYCLIC COMPOUN, P118
[9]   VALENCE-SHELL EXPANSION IN SULPHUR HETEROCYCLES [J].
SALMOND, WG .
QUARTERLY REVIEWS, 1968, 22 (03) :253-&
[10]  
SIDGWICK NV, 1966, ORGANIC CHEMISTRY NI, P642