Novel synthesis of 2,2-bis(2-methoxy-1-oxidodiazenyl)ethylnitramines via the relative ethyl trifluoroacetate
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1949
Novel synthesis of 2,2-bis(2-methoxy-1-oxidodiazenyl)ethylnitramines via the relative ethyl trifluoroacetate I. N. Zyuzin Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akademika Semenova, 142432 Chernogolovka, Moscow region, Russian Federation. E-mail: [email protected] A novel synthesis of 2,2-bis(2-methoxy-1-oxidodiazenyl)ethyl derivatives of methylnitramine and ethylenedinitramine consists in the treatment of 2,2-bis(2-methoxy-1-oxidodiazenyl) ethyl trifluoroacetate with the corresponding nitramines and N-ethyl-N,N-diisopropylamine. Key words: azoxy compounds, diazene oxides, 2-alkoxydiazene 1-oxides, methylnitramine, ethylenedinitramine, trifluoroacetates, nucleophilic substitution.
Alkoxy-NNO-azoxy compounds (AAC) (2-alkoxydiazene 1-oxides)1 are members of the chemotype of large class of azoxy compounds, which are increasingly used as promising components of high energy materials and as precursors for the preparation of novel energy-intensive heterocycles. 2—4 Another type of azoxy compounds, 1-(di)alkylamino-2-alkoxydiazene 1-oxides, is structurally the closest one to AAC.1,5,6 Its representatives are among the most efficient donors of nitric oxide, and currently, some of them are being actively evaluated as promising anticancer drugs. In the case of AAC, such a pronounced biological activity has not yet been revealed. Some AAC have been proposed as promising components of high energy materials.7—13 First of all, this is due to a higher enthalpy of their formation as compared to nitramines of the same elemental composition.14 Secondly, the simplest AAC are thermally more stable than dialkylnitramines of the same composition.15 Finally, AAC usually are chemically more inert.16—18 A combination of alkoxyazoxy groups with other energy-rich ones expands dramatically the opportunities to search for novel high energy compounds due to the increased number of possible hypothetical molecules of the same elemental composition. High energy compounds, whose molecules simultaneously contain alkoxyazoxy and nitramine groups, are of especial interest. There are three such compounds (1—3) known, as well as bimolecular compound 4. Compounds 1—3 have been proposed as components of composite solid rocket propellants (CSRP).7 Thermodynamic calculations have demonstrated7 that compounds 1—3 are of interest as gasifying components in compositions with a metal-free active binder and as such, they are slightly superior to 1,1-bis(methoxy-NNOazoxy)ethyl derivatives of high energy heterocycles.7,8,10,11 Since compound 2 is poorly soluble in the most of organic
solvents, it can be expected that it would be almost insoluble in the active binder of CSRP. This may be an additional advantage of compound 2 over other gasifying components of the CSRP. Compounds 1 and 2 were previously synthesized via the reaction of methylnitramine and ethylenedinitramine with O-derivatives of 2,2-bis(2-methoxy-1-oxidodiazenyl) ethanol (5a,b) and triethylamine in ethanol (Scheme 1).19
Published in Russian in Izvestiya Ak
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