N-chloro and N-bromosaccharins:: Valuable reagents for halogenation of electron rich aromatics and cohalogenation of alkenes

被引：37

作者：

de Souza, SPL ^{[1
]}

da Silva, JFM ^{[1
]}

de Mattos, MCS ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, Inst Quim, BR-21945970 Rio De Janeiro, Brazil

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2003年 / 14卷 / 05期

关键词：

cohalogenation; aromatic halogenation; N-halosaccharin;

D O I：

10.1590/S0103-50532003000500021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Chloro- and N-bromosaccharins react with electron rich aromatic compounds (anisole, acetanilide, N,N-dimethylaniline) producing halogenated compounds. The reaction with N-bromosaccharin gives para-substituted compounds only, whereas N-chlorosaccharin produces orto and para mixtures (para isomer predominantly, ca. 4-5:1). The reactions of the N-halosaccharins with alkenes (cyclohexene, styrene, alpha-methylstyrene, and 1-hexene) give the corresponding halohydrins.

引用

页码：832 / 835

页数：4

共 16 条

[1]

BACHHAWA.JM, 1973, INDIAN J CHEM, V11, P609

[2]

BACHHAWAT JM, 1971, INDIAN J CHEM, V9, P1335

[3]

CHAUHAN RPS, 1995, ASIAN J CHEM, V7, P667

[4] DETERMINATION OF SOME SULFUR-COMPOUNDS WITH N-BROMOIMIDES [J].

DAS, CM .

TALANTA, 1991, 38 (03) :347-350

[5] A green preparation of N-chloro- and N-bromosaccharin [J].

de Souza, SPL ;

da Silva, JFM ;

de Mattos, MCS .

SYNTHETIC COMMUNICATIONS, 2003, 33 (06) :935-939

[6]

Dolenc D, 2000, SYNLETT, P544

[7]

Khan MU, 1998, OXID COMMUN, V21, P362

[8]

MANIKYAMBA P, 1980, INDIAN J CHEM A, V19, P1122

[9]

MANOHARAN V, 1986, J INDIAN CHEM SOC, V63, P613

[10]

Mendonça GF, 2003, SYNTHESIS-STUTTGART, P45

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