Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

被引：29

作者：

Motherwell, WB ^{[1
]}

Greaney, MF ^{[1
]}

Tocher, DA ^{[1
]}

机构：

[1] UCL, Christopher Ingold Labs, Dept Chem, London WC1H OAJ, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 24期

关键词：

D O I：

10.1039/b209079a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of alpha-phenylsulfanyl esters 11-14 with one equivalent of difluoroiodotoluene 3a produced the alpha-fluoro sulfides 17-20 in good overall yield through a Fluoro-Pummerer reaction. A second equivalent of reagent produced alpha,alpha-difluoro sulfides and a third led to alpha,alpha-difluoro sulfoxides. An identical pattern of reactivity was observed with the alpha-phenylsulfanyl lactone 26. This sequential fluorination-oxidation behaviour was exploited in the one-pot synthesis of 3-fluoro-2(5H)-furanone 33 starting from alpha-phenylsulfanylbutyrolactone 32.

引用

页码：2809 / 2815

页数：7

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