Reactions of aminophenols with formaldehyde and hydrogen sulfide |
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| Authors: | V. R. Akhmetova G. R. Nadyrgulova S. R. Khafizova T. V. Tyumkina A. A. Yakovenko M. Yu. Antipin L. M. Khalilov R. V. Kunakova U. M. Dzhemileva |
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| Affiliation: | (1) Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075 Ufa, Russian Federation;(2) Ufa State Institute of Service, 145 ul. Chernyshevskogo, 450077 Ufa, Russian Federation;(3) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation |
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| Abstract: | The reaction of m-aminophenol with CH2O and H2S (1: 2: 1 ratio) afforded 2, 12-dioxa-4, 14-dithia-6, 16-diazatricyclo[15.3.1.17,11]docosa-1(20), 7(22), 8, 10, 17(21), 18-hexaene in ∼9% yield. Aminophenol o-and p-isomers react with CH2O and H2S (1: 3: 2) to form 2-and 4-[4H-1,3,5-dithiazin-5(6H)-yl]phenols in 86 and 71% yields, respectively. In the crystal structure of the latter, molecules contain dithiazine cycles in the chair conformation with the axial hydroxyphenyl group. Molecular packing represents a combination of molecules forming chains due to the OH...S intermolecular hydrogen bond. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 305–308, February, 2006. |
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| Keywords: | thiomethylation o-, m-, and p-aminophenols formaldehyde hydrogen sulfide X-ray diffraction analysis |
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