Synthesis 2015; 47(04): 533-537
DOI: 10.1055/s-0034-1378930
paper
© Georg Thieme Verlag Stuttgart · New York

Unprecedented Synthesis of 2H,6H-1,5-Dithiocines Reinvestigated: A Structural Corrigendum Revealing Isothiazole-3(2H)-thiones

Klaus Banert*
a   Technische Universität Chemnitz, Organic Chemistry, Strasse der Nationen 62, 09111 Chemnitz, Germany   Fax: +49(371)53121229   Email: klaus.banert@chemie.tu-chemnitz.de
,
Neeraj Singh
a   Technische Universität Chemnitz, Organic Chemistry, Strasse der Nationen 62, 09111 Chemnitz, Germany   Fax: +49(371)53121229   Email: klaus.banert@chemie.tu-chemnitz.de
,
Marcus Korb
b   Technische Universität Chemnitz, Inorganic Chemistry, 09107 Chemnitz, Germany
,
Heinrich Lang
b   Technische Universität Chemnitz, Inorganic Chemistry, 09107 Chemnitz, Germany
› Author Affiliations
Further Information

Publication History

Received: 22 September 2014

Accepted after revision: 18 October 2014

Publication Date:
17 November 2014 (online)


Dedicated to Professor Ernst Schaumann

Abstract

The synthesis of postulated 2H,6H-1,5-dithiocines from isonitriles and acetylenedicarboxylates or dibenzoylacetylene in the presence of elemental sulfur was repeated. The products do not possess the structure of eight-membered sulfur heterocycles, but isothiazole-3(2H)-thiones were formed instead. This structural corrigendum was confirmed not only by a critical consideration of the 13C NMR spectroscopic data and by the correction of the MS spectra and the values of the elemental analyses but also by X-ray crystallographic structure determination. Several reaction mechanisms are discussed to explain the generation of the observed isothiazole-3(2H)-thiones.

Supporting Information

 
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