Issue 46, 2009
From the journal:

Chemical Communications

Synthesis and rearrangement of a bridged thioamide†

Michal Szostaka  and  Jeffrey Aubé*a  

* Corresponding authors

a Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, Lawrence, Kaas 66045-785ns2, USA
E-mail: jaube@ku.edu
Fax: +1 785 864 4496
Tel: +1 785 864 5326

Abstract

The synthesis of a bridged thiolactam is described. This thiolactam is shown to undergo an unusual C–N bond cleavage reaction under conditions of its synthesis. Spectroscopic properties of the thiolactam indicate a considerable degree of twist of the thioamide bond.

Graphical abstract: Synthesis and rearrangement of a bridged thioamide

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Article information

DOI
https://doi.org/10.1039/B917508C
Article type
Communication
Submitted
25 Aug 2009
Accepted
08 Oct 2009
First published
30 Oct 2009

Chem. Commun., 2009, 7122-7124

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Synthesis and rearrangement of a bridged thioamide

M. Szostak and J. Aubé, Chem. Commun., 2009, 7122 DOI: 10.1039/B917508C

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