Nitration of 5-methyltetrazole
various starting materials such as 2-methylimidazole,
2-methoxy-2-methyl-imidazolidine-4,5-dione,and2-methylpyrimidine-4,6-dione(4,5-dihydroxy-2-methylpyrimidine) were nitrated and then hydrolyzed to give
FOX-7 by somewhat different process. Since the methyl group was converted to dinitromethylidene moiety in all methods, nitration of 5-methyltetrazole
was attempted to afford 5-dinitromethylidene-1,4-dihydrotetrazole. But this reaction failed to proceed, and most of the starting material was
recovered.
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With the necessary intermediates in hand, we sought to construct the N2FOX-7 using decarboxylation and elimination. Thus, various conditions were
tried. When ethyl 5-tetrazolyldinitro-acetate was treated with water, 5-dinitromethyltetrazole was readily given. Hydrolysis followed by
decarboxylation took place completely within 2 h at 50 °C.
Synthesis and Characterization of High EnergeticTetrazole and Furoxan Derivatives, (Korea)
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ethyltetrazolylacetate
N4HC-CH2-C(=O)-O-CH2CH3
The reason that the nitration of 5-methyltetrazole failed to proceed is probably the same reason that nitration of plain 1,2,3-triazole is essentially
impossible.* I suspect that the electron-withdrawing tetrazole ring pulls away electric charge from the methyl group, giving it a partial positive
charge and effectively shielding it from interaction with nitronium ions, which is the mechanism of reaction in most nitrations.
*In contrast, 4-nitro-1,2,3-triazole is easily both nitrated, and oxidized interestingly, by normal mixed HNO3/H2SO4 acids to
4,5-dinitro-1,2,3-triazole-N-oxide. The addition of one nitro group appears to activate the other CH to nitration.
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for this little golden nugget!
. I am reading a PDF here: http://www14.atpages.jp/~highenergy/hb_jx/File-hb-005-CESW20... . There is a chart comparing the promise between molecules composed only of
nitrogen atoms. The N60 molecule is the graphene of the energetic materials world. I watched the staircase implementation of the big bang theory and
in it Leonard is working on a new rocket fuel for the government with over 8,000,000 newtons of thrust. Leonard shows his friends the new fuel in his
apartment, however he fails to take into account that his rocket fuel was for a full scale rocket, and he mixes it in a tovex coated with Iridium and
exposes far too much of the propellant's surface area to the Iridium resulting in the accident seen on the big bang theory season 3 the staircase
implementation. Buy it on itunes and skip to around 17 minutes to see an awesome novel rocket fuel based on a real one developed in 2003.