Issue 9, 1990

2,5-Dihydro-1,2,3,5-thiatriazole1-oxides, 2H-1,2,3,5-thiatriazol-1-ium salts, and 2,5-dihydro-1,2,3,5-thiatriazol-5-yl radicals. X-Ray molecular structure of 2,5-dihydro-2,4-diphenyl-1,2,3,5-thiatriazole 1-oxide and 2,4-diphenyl-2H-1,2,3,5-thiatriazol-1-ium bromide

Abstract

N-Substituted amidrazones (4ag) react with thionyl chloride to give 2,5-dihydro-1,2,3,5-thiatriazole 1-oxides (5ag). X-Ray analysis of compound (5c) confirmed the 2,5-dihydro structure which is also the predominant tautomer in solution. Reaction of compounds (5ag) with phosphorus pentachloride or pentabromide led to the formation of yellow 2H-1,2,3,5-thiatriazol-1-ium salts (6ah), the structure being established by X-ray structure analysis of compound (6h). Reduction of compounds (6ah) in 1,2-dimethoxyethane with sodium or potassium metal readily generated 2,5-dihydro-1,2,3,5-thiatriazol-5-yl radicals (1ag) which were studied using ESR, EN DOR, and general triple resonance spectroscopy. The results led to a complete analysis and full assignment of all coupling constants.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1990, 1619-1626

2,5-Dihydro-1,2,3,5-thiatriazole1-oxides, 2H-1,2,3,5-thiatriazol-1-ium salts, and 2,5-dihydro-1,2,3,5-thiatriazol-5-yl radicals. X-Ray molecular structure of 2,5-dihydro-2,4-diphenyl-1,2,3,5-thiatriazole 1-oxide and 2,4-diphenyl-2H-1,2,3,5-thiatriazol-1-ium bromide

F. A. Neugebauer, H. Fischer, R. Crockett and C. Krieger, J. Chem. Soc., Perkin Trans. 2, 1990, 1619 DOI: 10.1039/P29900001619

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