The Open Organic Chemistry Journal

2008, 2 : 110-113
Published online 2008 December 3. DOI: 10.2174/1874095200801020110
Publisher ID: TOOCJ-2-110

Solid State and Solution Structure of an Unusual Compound Containing a CS Ring

Heribert Offermanns , Jürgen Martens , Martin Watzke , Peter Albers , Bernd Hannebauer , Matthias Janik , Arndt Müller , Kenneth Shankland , Charlotte K. Leech and Stewart F. Parker
Grünaustraße 2, D-63457 Hanau, Germany; E-mail: heppoff@gmx.de, AQura GmbH, Rodenbacher Chaussee 4, D-63457 Hanau, Germany; E-mail: peter.albers@aqura.de, ISIS Facility, Rutherford Appleton Laboratory, Chilton, Didcot, Oxon.

ABSTRACT

The structure of the product of the Asinger reaction of acetophenone with n-butylamine and elemental sulfur is still under debate. Two products have been proposed: a hexathiocanthione containing a C2S6 ring with an exocyclic thione and a heptathiocane containing a CS7 ring. A single crystal X-ray study has shown that the heptathiocane structure is correct. 1H and 13C NMR investigations in solution confirm that the structure is maintained in solution and that there is no evidence for the imine tautomer.