10425-71-5Relevant academic research and scientific papers
Chemistry of the Phenoxathiins and Isosterically Related Heterocycles. XXXII. The Synthesis of 2-Azathianthrene and Selected Analogs
Lam, Wing W.,Martin, Gary E.,Lynch, Vincent M.,Simonsen, Stanley H.,Lindsay, Charles M.,Smith, Keith
, p. 785 - 791 (2007/10/02)
The synthesis of 2-azathianthrene (benzodithiinopyridine), the only remaining monoazathianthrene yet to be reported, is described.Attempts at the direct condensation of disubstituted pyridines with the dianion of 1,2-dimercaptobenzene were generally unsuccessful requiring that the alternative condensation of the dianion with disubstituted pyridine 1-oxides be employed.The title compound was characterized by physical means including 13 C-nmr spectroscopy.One analog, 4-nitro-2-azathianthrene was also studied by X-ray crystallographic means; the molecule crystallized with two molecules in the asymetric unit P21/n, a=20.712(3), b=7.8109(13), c=13.720(2) Angstroem, β=107.880(11) deg, Z=8, the data refined to a final R=0.051 for 3061 reflections.Dihedral angles between the planes of the phenyl rings were 135.00(13) and 132.52(13) deg for the two independent molecules contained in the crystal.Close non-bonded S...O intramolecular contacts were observed in both molecules between the sulfur and nitro-group oxygens.Both nitro groups are twisted out the plane of the pyridine ring and are oriented at angles of 28.75 and 38.82 deg respectively.
