CONVERSION OF ALLYLIC PHENYLSELENIDES TO THE REARRANGED ALLYLIC CHLORIDES BY N-CHLOROSUCCINIMIDE - MECHANISM OF SELENIUM-CATALYZED ALLYLIC CHLORINATION OF BETA-PINENE

被引：95

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/jo01337a047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of diphenyl diselenide with NCS affords phenylselenenyl chloride (4) and iV-phenylseleno-succinimide (5). The latter proved to be an active catalyst for the allylic chlorination of β-pinene by iV-chlorosuccin-imide (NCS). While studying the mechanism of this catalytic chlorination, it was found that allylic phenylselenides are transformed by NCS to the rearranged allylic chlorides in high yield. A convenient method for the preparation of N-(phenylseleno)succinimide was developed. It was demonstrated that an allylic phenylselenide affords the rearranged allylic sulfonamide upon treatment with anhydrous Chloramine-T. © 1979, American Chemical Society. All rights reserved.

引用

页码：4208 / 4210

页数：3

共 12 条

[1] SELENIUM-CATALYZED NONRADICAL CHLORINATION OF OLEFINS WITH N-CHLOROSUCCINIMIDE [J].