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Chemistry of the phenoxathiins and isosterically related heterocycles. 32. The synthesis of 2-azathianthrene and selected analogs [Novel Heterocyclic Systems. 24]

Lam, Wing W., Martin, Gary E., Lynch, Vincent M., Simonsen, Stanley H., Lindsay, Charles M. and Smith, Keith 1986. Chemistry of the phenoxathiins and isosterically related heterocycles. 32. The synthesis of 2-azathianthrene and selected analogs [Novel Heterocyclic Systems. 24]. Journal of Heterocyclic chemistry 23 (3) , pp. 785-791. 10.1002/jhet.5570230327

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Abstract

The synthesis of 2-azathianthrene ([1,4]benzodithiino[2,3-c]pyridine), 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 13C-nmr spectroscopy. One analog, 4-nitro-2-azathianthrene was also studied by X-ray crystallographic means; the molecule crystallized with two molecules in the asymmetric unit P21/n, a = 20.712(3), b = 7.8109(13), c = 13.720(2)Å, β = 107.880(11)°, 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)° for the two independent molecules contained in the crystal. Close nonbonded S ⃛O intramolecular contacts were observed in both molecules between the sulfur and nitro-group oxygens. Both nitro groups are twisted out of the plane of the pyridine ring and are oriented at angles of 28.75 and 38.82° respectively.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: For the previous paper in this series, see: S. Puig-Torres, G. E. Martin, S. B. Larson and S. H. Simonsen, J. Heterocyclic Chem., 21, 995 (1984); This work also represents Part 24 in the series Novel Heterocyclic Systems. For the previous paper in this series, see ref [32].
Publisher: Wiley
ISSN: 0022-152x
Last Modified: 04 Jun 2017 02:57
URI: http://orca.cf.ac.uk/id/eprint/14540

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