SUBSTITUENT EFFECTS OF CHLORINE IN NORBORNANES

被引：20

作者：

FRY, AJ

FARNHAM, WB

机构：

[1] Chemistry Department, Wesleyan University, Middletoum

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 08期

关键词：

D O I：

10.1021/jo01260a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrochlorinations of 1-chloronorbornene (5) and 2-chloronorbornene (6) afford 1,exo-3-dichloronorbornane (4) and 2,2-dichloronorbornane (2), respectively. Solvolytic and silver ion promoted ionization of 2, 4, and l,exo-2-dichloronorbornane (3) have been examined. The results do not require the assumption of bridged intermediates. Hydroboration of 5, followed by oxidation with alkaline hydrogen peroxide, results in a mixture of 1-chloro-exo-2-norbornanol (11, 38%) and 1-chloro-exo-3-norbornanol (12, 62%); this orientation differs from that observed in hydroboration of other allylic chlorides. © 1969, American Chemical Society. All rights reserved.

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页码：2314 / &

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