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Synthesis of thiadiazabicyclane and bis-1,3,5-dithiazinane by cyclothiomethylation of aliphatic diamines with CH2O and H2S |
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| Authors: | Vnira R. Akhmetova Guzel R. Nadyrgulova Tat'yana V. Tyumkina Mikhail Yu. Antipin Usein M. Dzhemilev |
| Affiliation: | a Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, 450075 Ufa, Russian Federation b A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov str., 119991 Moscow, Russian Federation c Ufa State Academy of Economics and Service, 145 Chernyshevskii str., 450077 Ufa, Russian Federation |
| Abstract: | Cyclocondensation of aliphatic diamines with CH2O and H2S (1:3:2 ratio, 0 °C) was carried out to give thiadiazabicyclanes and dithiadiazabicyclanes (1:6:4 ratio), which were previously difficult to synthesize. Symmetric α,ω-bis-1,3,5-dithiazinanes were synthesized at 80 °C by this reaction. The stereochemistry of thiadiazabicyclanes was assigned by 1H and 13C NMR spectroscopy and by theoretical DFT calculations, and of bis-dithiazinanes by X-ray diffraction study in the solid state. |
| Keywords: | Thiadiazabicyclane bis-1,3,5-Dithiazinane Cyclothiomethylation Aliphatic diamines N,S-Containing heterocycles Formaldehyde Hydrogen sulfide X-ray crystal analysis |
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