SELENIUM-CATALYZED NONRADICAL CHLORINATION OF OLEFINS WITH N-CHLOROSUCCINIMIDE

被引：66

作者：

HORI, T ^{[1
]}

SHARPLESS, KB ^{[1
]}

机构：

[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 23期

关键词：

D O I：

10.1021/jo01337a046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arylselenenyl chlorides (ArSeCl) or aryl di-selenides (ArSeSeAr) were effective as catalysts for the chlorination of olefins with N-chlorosuccinimide. The principal product is a rearranged allylic chloride, and the vinyl chloride is usually a minor product. Another method for nonradical allylic chlorination of olefins involves reaction of the olefin with TsN―S―O and N-chloro-succinimide and affords the unrearranged allylic chloride as the major product. © 1979, American Chemical Society. All rights reserved.

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页码：4204 / 4208

页数：5

相关论文

共 30 条

[1] MAJOR IMPROVEMENT IN OSMIUM CATALYZED VICINAL HYDROXYLATION OF OLEFINS BY TERT-BUTYL HYDROPEROXIDE [J].

AKASHI, K ;

PALERMO, RE ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :2063-2066

[2] ORGANIC HYPOHALITES [J].

ANBAR, M ;

GINSBURG, D .

CHEMICAL REVIEWS, 1954, 54 (06) :925-958

[3] SELENIUM DIOXIDE OXIDATIONS OF OLEFINS - TRAPPING OF ALLYLIC SELENINIC ACID INTERMEDIATE AS A SELENINOLACTONE [J].

ARIGONI, D ;

VASELLA, A ;

SHARPLES.KB ;

JENSEN, HP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (23) :7917-7919

[4] HALOGENATION OF SATURATED COMPOUNDS WITH N-CHLORO-SUCCINIMIDE AND N-BROMO-SUCCINIMIDE [J].

BUUHOI, NP ;

DEMERSEMAN, P .

JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (06) :649-652

[5]

DELAMARE PBD, 1976, ELECTROPHILIC HALOGE, pCH6

[6]

HEBELYNCK MF, 1949, EXPERIENTIA, V5, P69

[7] OSMIUM-CATALYZED VICINAL OXYAMINATION OF OLEFINS BY N-CHLORO-N-ARGENTOCARBAMATES [J].

HERRANZ, E ;

BILLER, SA ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (11) :3596-3598

[8] IMPROVEMENTS IN OSMIUM-CATALYZED OXYAMINATION OF OLEFINS BY CHLORAMINE-T [J].

HERRANZ, E ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2544-2548

[9] ALLYLIC DEUTERATION AND TRITIATION OF OLEFINS WITH N-SULFINYLSULFONAMIDES [J].

HORI, T ;

SINGER, SP ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (07) :1456-1459

[10] CONVERSION OF ALLYLIC PHENYLSELENIDES TO THE REARRANGED ALLYLIC CHLORIDES BY N-CHLOROSUCCINIMIDE - MECHANISM OF SELENIUM-CATALYZED ALLYLIC CHLORINATION OF BETA-PINENE [J].

HORI, T ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4208-4210