1H NMR-based kinetic and mechanistic study of unusual skeletal rearrangements of a spirobornyl tosylate derivative

被引：1

作者：

Lobb, Kevin A. ^{[1
]}

Kaye, Perry T. ^{[1
]}

机构：

[1] Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2011年 / 24卷 / 01期

基金：

新加坡国家研究基金会;

关键词：

mechanistic study; skeletal rearrangements; spirobornyl tosylate; RACEMIZATION;

D O I：

10.1002/poc.1699

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

H-1 NMR analysis of the kinetics of skeletal rearrangement of optically pure 3,3-xylyl-2-exo-bornyl tosylate in CDCl3 indicates the operation of tandem autocatalytic and pseudo-first-order transformations, leading sequentially to a pair of isomeric camphene derivatives and involving partial racemization. Changing the solvent system has been shown to permit the chemoselective isolation of either of the isomeric camphenes. Copyright (C) 2010 John Wiley & Sons, Ltd.

引用

页码：38 / 44

页数：7

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