On the reaction of chlorodithiophosphoric acid pyridiniumbetaine with polyfunctional nucleophiles: Part II. Reaction with thiosemicarbazide derivatives |
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| Institution: | 1. A.M. Butlerov Institute of Chemistry, Kazan Federal University, Kremlevskaya str. 18, Kazan 420008, Russia;2. A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str. 8, Kazan 420088, Russia;1. Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal;2. Centro de Química e Bioquímica, DQB and BioISI – Biosystems & Integrative Sciences Institute, Faculdade de Ciências da Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal;1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmans’ka str., Kyiv 02660, Ukraine;2. Department of Organic Chemistry, National Technical University of Ukraine ‘Kyiv Polytechnic Institute’, 37, Prospect Peremogy, Kyiv 03056, Ukraine;1. Nuclear Fuel Cycle Research Theme, Australian Nuclear Science and Technology Organisation, Locked Bag 2001, Kirrawee DC, NSW 2232, Australia;2. Mark Wainwright Analytical Centre, University of New South Wales, Kensington, NSW 2052, Australia;3. School of Physics and the Australian Institute for Nanoscale Science and Technology, University of Sydney, NSW 2006, Australia;1. Erciyes University, Faculty of Science, Department of Chemistry, 38039 Kayseri, Turkey;2. Inönü University, Faculty of Science and Arts, Department of Chemistry, 44280 Malatya, Turkey |
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| Abstract: | Chlorodithiophosphoric acid pyridiniumbetaine, PyPS2Cl (I), reacts with thiosemicarbazide derivatives (RNH)(H2NNMe)CS, R= iso-propyl, tert-butyl, in acetonitrile in the absence of any HCl-acceptor to form new compounds with a five-membered heterocycle, i.e. 5-iso-propylamino-4-methyl-2-sulfido-2-thioxo-1,3,4,2λ5-thiadiazaphospholan-5-onium (II) or 5-tert-butylamino-4-methyl-2-sulfido-2-thioxo-1,3,4,2λ5-thiadiazaphospholan-5-onium (III). The triethylammonium salt of 1,3-bis-(N-methyl-N′-tert-butyl-thioureido)-2,4-disulfido-2,4-dithioxo-1,3-diaza-2λ5,4λ5-diphosphetidine (IV) is formed when the reaction is carried out in the presence of triethylamine. The prepared compounds were characterized by 31P NMR, FT-IR spectroscopies, mass spectrometry and the molecular structures of II, III and IV were determined by X-ray crystallography. |
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