IRON(II)-MEDIATED REARRANGEMENT OF 1,2,4-TRIOXANES INTO 1,2-DIOL MONOESTERS VIA 1,5-HYDROGEN TRANSFER

被引：32

作者：

BLOODWORTH, AJ

SHAH, A

机构：

[1] Chemistry Department, University College London, London, WC1H 0AJ

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 41期

关键词：

D O I：

10.1016/0040-4039(95)01530-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Five 3-alkyl- or 3-aryl-5,5,6,6-tetramethyl-1,2,4-trioxanes 4 upon treatment with iron(II) sulfate in aqueous acetonitrile under nitrogen for 12-72h are cleanly isomerised into the corresponding 2,3-dimethylbutan-2,3-diol monoesters 5; it is suggested that the reactions involve reduction to oxyl radicals followed by 1,5-hydrogen transfer, a sequence that has recently been implicated in the molecular mechanism of action of the antimalarial artemisinin.

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页码：7551 / 7554

页数：4

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