REEXAMINATION OF THE THERMOLYTIC REARRANGEMENT OF 4-HALOPHENYL AZIDES TO 2-AMINOPHENOLS AND OTHER PRODUCTS

被引:23
作者
GERSHON, H [1 ]
CLARKE, DD [1 ]
GERSHON, M [1 ]
机构
[1] NEW YORK BOT GARDEN, BRONX, NY 10458 USA
来源
MONATSHEFTE FUR CHEMIE | 1993年 / 124卷 / 04期
关键词
ACETYLATED-2-AMINO-5-HALOPHENOLS; 2-ACETAMIDO-5-HALOANISOLES; 6-HALO-2-METHYLBENZOXAZOLES; 6-HALOBENZOXAZOLONES; 6-HALOTRIACETYLAMINOPHENOLS; H-1-NMR SPECTRA; FUNGICIDAL ACTIVITY;
D O I
10.1007/BF00814133
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The halogenation of derivatives of 2-aminophenol with N-chloro- and N-bromosuccinimides at ambient temperatures in acetic acid was studied. With the necessary compounds available, a reexamination of the thermolytic rearrangement of 2-halophenyl azides to 2-aminophenols and other products was undertaken. It is certain that the rearrangement of 4-halophenyl azides to 2-aminophenols occurs but the products identified in this study differ significantly from those reported previously by Suschitzky et al. (1963, 1966).
引用
收藏
页码:367 / 379
页数:13
相关论文
共 30 条
[1]  
ALIEV NA, 1980, FUNGTISIDY, V46
[2]   EFFECT OF SUBSTITUENTS IN THE FORMATION OF DIACETANILIDES [J].
AYYANGAR, NR ;
SRINIVASAN, KV .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (07) :1292-1296
[3]  
BUUHOI NP, 1944, LIEBIGS ANN CHEM, V556, P1
[4]   THE ANALGESIC ACTIVITY OF SOME BENZOXAZOLONE DERIVATIVES [J].
CLOSE, WJ ;
TIFFANY, BD ;
SPIELMAN, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (04) :1265-1268
[5]   A new method of reducing aromatic nitro-compounds [J].
de Kiewiet, TE ;
Stephen, H .
JOURNAL OF THE CHEMICAL SOCIETY, 1931, :82-84
[6]   The unsaturation and tautomeric mobility of heterocyclic compounds Part XI alpha- and beta-naphthoxazole and 5-bromobenzoxazole derivatives - The ultra-violet absorption spectra of some tautomeric selenazoles [J].
Desai, RD ;
Hunter, RF ;
Khalidi, ARK .
JOURNAL OF THE CHEMICAL SOCIETY, 1938, :321-329
[7]  
DIEPOLDER E, 1911, CHEM BER, V44, P2498
[8]  
ECKSTEIN Z., 1958, Przemysl Chemiczny, V37, P418
[9]   SYNTHESES OF HETEROCYCLIC COMPOUNDS .14. OXAZOLES FROM PYROLYSIS OF ARYL AZIDES IN A MIXTURE OF A CARBOXYLIC AND POLYPHOSPHORIC ACID [J].
GARNER, R ;
MULLOCK, EB ;
SUSCHITZ.H .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (21) :1980-&
[10]   ELECTROPHILIC HALOGENATION OF 8-METHOXYQUINOLINE [J].
GERSHON, H ;
MCNEIL, MW ;
SCHULMAN, SG .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (25) :4078-4082