Synthesis and study of organic nitrates of heterofunctional series. 5. Synthesis of 3,3-bis(hydroxymethyl)oxetane mono- and dinitrates and 2,2-bis(hydroxymethyl)propane-1,3-diol (pentaerythritol) mono- and dinitrates |
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| Authors: | Korolev A M Eremenko L T Meshikhina L V Eremenko I L Aleksandrov G G Konovalova N P Lodygina V P |
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| Institution: | (1) Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation;(2) N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991 Moscow, Russian Federation |
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| Abstract: | New procedures were developed for the synthesis of 3,3-bis(hydroxymethyl)oxetane dinitrate (1) by O-nitration of the corresponding glycol (3) or its mononitrate (6), which were prepared by the reactions of 2,2-bis(hydroxymethyl)propane-1,3-diol (pentaerythritol) (2) mono- (4) and dinitrates (5), respectively, with alkali. A new method was devised for the synthesis of compounds 4 and 5 by the reaction of tetraol 2 with concentrated HNO3 in dichloroethane. The structures of compounds 1 and 6 were established by X-ray diffraction analysis. |
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| Keywords: | 3 3-bis(hydroxymethyl)oxetane 3 3-bis(hydroxymethyl)oxetane mono- and dinitrates O-nitration 2 2-bis(hydroxymethyl)propane-1 3-diol (pentaerythritol) 2 2-bis(hydroxymethyl)propane-1 3-diol (pentaerythritol) mono- and dinitrates heterocyclization X-ray diffraction analysis IR 1H and 13C NMR spectra |
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