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Paper | Regular issue | Vol 75, No. 1, 2008, pp.119-129
Published online, 28th September, 2007
DOI: 10.3987/COM-07-11191
1H NMR Sulfinyl Group Substituent Effects of Dithiinodiazine S-Oxides as a Key for Structure Assignment of Parent Dithiinodiazines

Andrzej Maslankiewicz,* Maria J. Maslankiewicz, Andrzej Zieba, and Krzysztof Marciniec

*Department of Organic Chemistry, The Medical University of Silesia, Jagielloñska 4, 41-200 Sosnowiec, Poland


1,4-Dithiinodipyridine 1 was prepared by reduction of 4-chloro-3-chlorosulfonylopyridine (8) with HI / H3PO3 system. Sulfur-assisted thermal isomerization of 1 resulted in a mixture of 1 and 2. Treatment of dithiinodiazines 1, 2, 5, and 6 with a nitrating mixture led almost selectively to respective S-monooxides 1a, 2a, 5a, and 6a. Due to the significant values of sulfinyl group substituent effects, 1H NMR spectra of 1,4-dithiino-S-oxides 1a, 2a, 5a, and 6a permitted for structure assignment of parent dithiins 1, 2, 5, and 6 and confirmed regioselectivity of the reaction of dithiins 1, 2, 5, and 6 with nitrating mixture.