Issue 13, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Conversion of (Z)-1,4-dihydroxyalk-2-enes into 2,5-dihydrofurans and of alkane-1,4-diols into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas formed by their copper(i)-mediated reactions with dicyclohexylcarbodiimide†

Michael G. Duffya  and  David H. Grayson*a  

* Corresponding authors

a University Chemical Laboratory, Trinity College, Dublin 2, Ireland

Abstract

(Z)-1,4-Dihydroxyalk-2-enes react with dicyclohexylcarbodiimide in the presence of catalytic amounts of copper(I) chloride to give O-alkyl monoisoureas which cyclise to give 2-substituted-2,5-dihydrofurans and dicyclohexylurea when they are treated with trifluoroacetic acid. Alkane-1,4-diols likewise give O-alkyl monoisoureas which cyclise to yield tetrahydrofurans.

Graphical abstract: Conversion of (Z)-1,4-dihydroxyalk-2-enes into 2,5-dihydrofurans and of alkane-1,4-diols into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas formed by their copper(i)-mediated reactions with dicyclohexylcarbodiimide

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Article information

DOI
https://doi.org/10.1039/B203389P
Article type
Paper
Submitted
05 Apr 2002
Accepted
24 May 2002
First published
10 Jun 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1555-1563

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Conversion of (Z)-1,4-dihydroxyalk-2-enes into 2,5-dihydrofurans and of alkane-1,4-diols into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas formed by their copper(I)-mediated reactions with dicyclohexylcarbodiimide

M. G. Duffy and D. H. Grayson, J. Chem. Soc., Perkin Trans. 1, 2002, 1555 DOI: 10.1039/B203389P

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