89181-72-6Relevant academic research and scientific papers
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
Korolev,Eremenko,Meshikhina,Eremenko,Aleksandrov,Konovalova,Lodygina
, p. 1859 - 1863 (2007/10/03)
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 HNO 3 in dichloroethane. The structures of compounds 1 and 6 were established by X-ray diffraction analysis.
Clean nitrations: Novel syntheses of nitramines and nitrate esters by nitrodesilylation reactions using dinitrogen pentoxide (N2O5)
Millar, Ross W.,Philbin, Simon P.
, p. 4371 - 4386 (2007/10/03)
In this novel nitration method dinitrogen pentoxide (N2O5) in an inert solvent is used as the nitrating agent, thereby removing the need for strong acids as the reaction medium. The N2O5 cleaves heteroatom-silicon bonds, in silylamines and silyl ethers respectively, to yield the desired energetic groupings (nitramines or nitrate esters respectively) without liberation of acids which would occur with conventional substrates (amines or alcohols). These nitrodesilylation reactions proceed cleanly and in good yield, and the scope of the reaction is illustrated by 29 examples, some of which produce high energy compounds, notably plasticisers and an energetic polymer precursor. These reactions are therefore potentially clean nitrations for the manufacture of energetic compounds which will minimise the impact of this activity on the environment in the future.
Preparation of di- and polynitrates by ring-opening nitration of oxetanes by dinitrogen pentoxide (N2O5)
Golding,Millar,Paul,Richards
, p. 7051 - 7062 (2007/10/02)
Ten oxetanes bearing various substituents were reacted with N2O5 in chlorinated hydrocarbon solvents to yield 1,3-dinitrate esters (I) by ring-opening nitration. The yields ranged from 73 to 88% for di-/trinitrates derived from oxetanes unsubstituted in the 2-position, to only 15 to 21% for oxetanes bearing such substituents. Although selective ring cleavage of oxetanes bearing non-hydroxylic substituents (epoxy (oxiranyl), spiro-oxetane and alkene) was not, in general, possible, selective nitration of hydroxyalkyloxetanes was achievable under the conditions employed to yield nitrato-methyloxetanes useful as precursors for energetic polyethers. A semi-quantitative reactivity comparison with representative epoxides indicated that the reactivity of oxetanes towards N2O5 was lower, as expected on account of their lower ring strain.
