Stereochemistry of organophosphorus cylic compounds—XV: Synthesis of tetramethylammonium salt of 2-oxo-2-thio-1,3,2,-oxazaphosphorinan and its crystal and molecular structures |
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Authors: | M Mikołajczyk J Omelanczuk WS Abdukakharov A Miller MW Wieczorek J Karolak-Wojciechowska |
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Institution: | Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Organic Sulphur Compounds, 90-362 ?odz, Boczna 5, Poland;Institute of General Chemistry, Technical University, 90-924 ?odz, Zwirki 36, Poland |
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Abstract: | 2-Hydroxy-1,3,-2-oxazaphosphorinan-2-thione (5) was prepared by alkaline hydrolysis of 2-chloro-1,3,2-oxazaphosphorinan-2- thione (6). Treatment of the latter with sodium methoxide afforded the 2-methoxy-derivative 7 from which the tetramethylammonium salt of the thioacid 5 was obtained by the action of trimethylamine. The structure of this salt has been determined by the direct method and refined by least-squares to R = 0.0734, a = 12.303(4), b = 9.041(3), c = 10.419(2) Å, space group P212121. The 2-oxo-2-thio-1,3,2-oxazaphosphorinanyl anion is in the chair form with the exocylic S and O atoms in an axial and equatorial position, respectively. An intermolecular H-bond between S and the endo-cyclic N atom is present in the solid-state structure. |
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