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.

引用

页码：4204 / 4208

页数：5

共 30 条

[21] HIGH STEREOSELECTIVITIES AND REGIOSELECTIVITIES IN TRANSITION-METAL CATALYZED EPOXIDATIONS OF OLEFINIC ALCOHOLS BY TERT-BUTYL HYDROPEROXIDE
SHARPLES.KB
MICHAELS.RC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (18) : 6136 - 6137
[22] ALLYLIC AMINATION OF OLEFINS AND ACETYLENES BY IMIDO SELENIUM-COMPOUNDS
SHARPLESS, KB
HORI, T
TRUESDALE, LK
DIETRICH, CO
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (01) : 269 - 271
[23] ALLYLIC AMINATION OF OLEFINS AND ACETYLENES BY IMIDO SULFUR-COMPOUNDS
SHARPLESS, KB
HORI, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (01) : 176 - 177
[24] SELENIUM DIOXIDE OXIDATION OF OLEFINS - EVIDENCE FOR INTERMEDIACY OF ALLYLSELENINIC ACIDS
SHARPLESS, KB
LAUER, RF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) : 7154 - +
[25] OSMIUM CATALYZED VICINAL HYDROXYLATION OF OLEFINS BY TERT-BUTYL HYDROPEROXIDE UNDER ALKALINE CONDITIONS
SHARPLESS, KB
AKASHI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (07) : 1986 - 1987
[26] OLEFIN SYNTHESIS - RATE ENHANCEMENT OF ELIMINATION OF ALKYL ARYL SELENOXIDES BY ELECTRON-WITHDRAWING SUBSTITUENTS
SHARPLESS, KB
YOUNG, MW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (07) : 947 - 949
[27] OSMIUM-CATALYZED VICINAL OXYAMINATIONS OF OLEFINS BY CHLORAMINE-T
SHARPLESS, KB
CHONG, AO
OSHIMA, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (01) : 177 - 179
[28] ALLYLIC OXIDATION OF OLEFINS BY CATALYTIC AND STOICHIOMETRIC SELENIUM DIOXIDE WITH TERT-BUTYL HYDROPEROXIDE
UMBREIT, MA
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (16) : 5526 - 5528
[29] VILSMAIER E, 1971, LIEBIGS ANN CHEM, V747, P151
[30] POSITIVE HALOGEN COMPOUNDS .3. ALLYLIC CHLORINATION WITH TERT-BUTYL HYPOCHLORITE - STEREOCHEMISTRY OF ALLYLIC RADICALS
WALLING, C
THALER, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (18) : 3877 - &

← 1 2 3 →