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Paper | Special issue | Vol 88, No. 2, 2014, pp.1397-1431
Published online, 11th November, 2013
DOI: 10.3987/COM-13-S(S)109
Synthesis and Reactions of 1,3,4-Selenadiazines

Wolf-Diethard Pfeiffer,* Harald Roßberg, Nazken Kelzhanova, Amanzhan T. Saginayev, Alexander Villinger, and Peter Langer*

*Institute of Chemistry, University of Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany


Various 1,3,4-selenadiazines were prepared by cyclization of selenosemicarbazides with phenacyl bromides. The compounds generally exist in their 6H-tautomeric form and contain an exocyclic imino group in the solid state. 1,3,4-4H-Selenadiazines, available from 1,2-dimethylated selenosemicarbazides, cannot be isolated because they rapidly undergo a deselenation reaction under the conditions of their formation. Deselenation can be induced for 1,3,4-6H-selenadiazines under forcing conditions by reflux of a solution in glacial acetic acid. On the other hand, a ring contraction is observed when concentrated HCl or HBr is used.