Issue 17, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Influence of ring size on the outcome of sulfide contraction reactions with thiolactams. Isolation of bicyclic ketene S,N-acetals and thioisomünchnones

Joseph P. Michael,*a   Charles B. de Koning,a   Christiaan W. van der Westhuyzena  and  Manuel A. Fernandesa  

* Corresponding authors

a Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, 2050 South Africa
E-mail: jmichael@aurum.chem.wits.ac.za

Abstract

Reaction between diethyl bromomalonate and 3-phenylpyrrolidine-2-thione yielded a vinylogous urethane by the Eschenmoser sulfide contraction. However, with 3-substituted piperidine-2-thiones, sulfur was retained in the products, and a range of bicyclic heterocycles, including bicyclic ketene S,N-acetals (2-alkylidene-1,3-thiazolidin-4-ones) and stable thioisomünchnones, was isolated. A novel dimeric ketene S,N-acetal was characterised by X-ray crystallography.

Graphical abstract: Influence of ring size on the outcome of sulfide contraction reactions with thiolactams. Isolation of bicyclic ketene S,N-acetals and thioisomünchnones

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Article information

DOI
https://doi.org/10.1039/B103560F
Article type
Paper
Submitted
20 Apr 2001
Accepted
20 Jun 2001
First published
03 Aug 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2055-2062

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Influence of ring size on the outcome of sulfide contraction reactions with thiolactams. Isolation of bicyclic ketene S,N-acetals and thioisomünchnones

J. P. Michael, C. B. de Koning, C. W. van der Westhuyzen and M. A. Fernandes, J. Chem. Soc., Perkin Trans. 1, 2001, 2055 DOI: 10.1039/B103560F

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