ACID-CATALYZED RACEMIZATION OF 1-(HETEROCYCLYLOXY)-2,3-PROPANEDIOLS

被引：10

作者：

BARLOW, JJ ^{[1
]}

BLOCK, MH ^{[1
]}

HUDSON, JA ^{[1
]}

LEACH, A ^{[1
]}

LONGRIDGE, JL ^{[1
]}

MAIN, BG ^{[1
]}

NICHOLSON, S ^{[1
]}

机构：

[1] ICI PLC,ALDERLEY PK,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 19期

关键词：

D O I：

10.1021/jo00045a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of enantiomerically pure heterocyclic ketals 5 have been prepared, and their acid-catalyzed hydrolysis to the corresponding diols 6 has been studied. During this reaction a rearrangement may occur to give racemic products, and so the kinetics of the two competing reactions have been studied to establish optimum conditions. The rate of rearrangement is independent of pH below the pK(a) of the heterocycle, whereas the rate of ketal continues to increase as pH is lowered. Brief treatment with strong acid has allowed the formation of very pure diols in high yield.

引用

页码：5158 / 5162

页数：5

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