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Issue 3, 1996
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Synthesis, hydrolysis reactions and conformational study of 2-substituted 3,5-diamino-4-nitroso-2H-1,2,6-thiadiazine 1,1-dioxides

Abstract

The 2-substituted 3,5-diamino-4-nitroso-2H-1,2,6-thiadiazine 1,1-dioxides are present in solution as a mixture of two rotational conformers of the nitroso group that are stabilized by hydrogen bonds with the amino groups in positions 3 and 5. The stability of these conformations has been studied using 1H, 13C and 15N NMR spectroscopy, as well as molecular orbital ab initio calculations. In addition, hydrolysis reactions of these compounds have been carried out affording 5-amino-4-hydroxyimino-3-oxo-3,4-dihydro-2H-1,2,6-thiadiazine 1,1-dioxides and 4-amino-3-oxo-2,3-dihydro-1,2,5-thiadiazole 1,1-dioxides.

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Article type: Paper
DOI: 10.1039/P29960000293
Citation: J. Chem. Soc., Perkin Trans. 2, 1996,0, 293-297
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    Synthesis, hydrolysis reactions and conformational study of 2-substituted 3,5-diamino-4-nitroso-2H-1,2,6-thiadiazine 1,1-dioxides

    I. Alkorta, C. García-Gómez, J. L. G. de Paz, M. L. Jimeno and V. J. Arán, J. Chem. Soc., Perkin Trans. 2, 1996, 0, 293
    DOI: 10.1039/P29960000293

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