Issue 24, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

William B. Motherwell,*a   Michael F. Greaney†a  and  Derek A. Tochera  

* Corresponding authors

a Department of Chemistry, Christopher Ingold Laboratories, University College London, 20 Gordon Street, London, UK
E-mail: w.b.motherwell@ucl.ac.uk
Fax: 44 20 7679 7524
Tel: 44 20 767 97533

Abstract

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

Graphical abstract: Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

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Article information

DOI
https://doi.org/10.1039/B209079A
Article type
Paper
Submitted
18 Sep 2002
Accepted
06 Nov 2002
First published
22 Nov 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2809-2815

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Fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

W. B. Motherwell, M. F. Greaney and D. A. Tocher, J. Chem. Soc., Perkin Trans. 1, 2002, 2809 DOI: 10.1039/B209079A

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