Madandcrazy
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nitro groups using double bounds
How prepared a energetic material which used a double bound between the nitrogen and the carbon atom ?
example is the
C=NNO2
and with which chemicals is it realizable ?
Contingently used starting materials and more than one chemical. (amides, amines and acids) ?
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simply RED
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Nitramide plus ketone may give the desired structure.
H2N-NO2 + R2C=O = R2C=N-NO2 + H2O
Nitrating guanidine (to (NH2)2C=N-NO2) is also a possible idea.
The geometry of =N-NO2 is quite interesting. It should be a planar structure.
.......O...O
.........N
......../
....=N
.........: (electron pair)
]
[Edited on 2-1-2006 by simply RED]
When logic and proportion have fallen sloppy dead...
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Marvin
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The 'standard' method for nitrimines is to react a diazoalkane with excess nitric oxide.
Carbonyl+nitramine might work for a few specific cases.
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Axt
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| Quote: | Originally posted by simply RED
Nitramide plus ketone may give the desired structure.
H2N-NO2 + R2C=O = R2C=N-NO2 + H2O
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| Quote: | Originally posted by Marvin
Carbonyl+nitramine might work for a few specific cases. |
Selected extracts from J. W. Suggitt et. al.; J. Org. Chem.; 1947; 12(3); 373-378.
"<i>We have succeeded in preparing furfuralnitrimine by the simple condensation of furfural with nitramide without catalyst or solvent. The
reaction would not take place with solvent present.
Furfuralnitrimine is reasonably stable (for a furan) when it is dry and, in fact, is best purified by sublimation at 100°.
No other aldehyde or ketone was found to condense with nitramide.</i>"
One for ketonitrimines that on the surface looks simple is from J. P. Freeman.; Chem. Rev.; 1973; 73(4); 283-292
"<i>There is at least one report of an a-ketonitrimine prepared by the action of a nitrite ester on a ketone in the presence of excess base, a
reaction in which the derived a-oximino ketone undergoes further nitrosation.</i>"
The parent ketone isn't mentioned, references to T. Matsumoto and S. Yasuda, Tetrahedron Lett., 5311 (1968).
Nitroguanidine, normally shown as H2N-C(=NH)-NH-NO2 was actually shown to be H2N-C(=NNO2)-NH2.
The Infrared Spectra of Nitroguanidine and Related Compounds
W. D. Kumler
J. Am. Chem. Soc.; 1954; 76(3); 814-816.
[Edited on 10-1-2006 by Axt]
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Madandcrazy
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May be a nucleophilic addition with neutral bindings of a amide and a carbonyl-component or a ketone in acidic environment to realizing a nitrated
imin.
O=CH-NNO2-CH2-NNO2-CH2-NH2
or
OH-CH2-NNO2-CH2-NNO2-CH2-NH2
-->
(CH2)3(NNO2)2C=NO2
Attractive to this question probably the
C=N-NO2 or C-N(NO2)2 nitro groups.
[Edited on 11-1-2006 by Madandcrazy]
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Madandcrazy
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Corrective to the last post anymore possible formulas to the synthesis for the diazine derivat and the binding to the nitrogen.
(CH2)2(NNO2)2C=NNO2
>CH2-NNO2-CH2-NNO2-C=NNO2>
and
(CH2)2(NNO2)2C-N(NO2)2
>CH2-NNO2-CH2-NNO2-C-N(NO2)2>
Surely a good way for a triazine  synthesis.
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Madandcrazy
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To the topic some more of a eventually possible additional
synthesis of a diazine, triazine or a nitated ketamin by a imin synthesis with the -N(NH2)2 group and a ketone.
=CH-CH2-2(NNO2)2C[H-NO2]
>=CH-NNO2-CH2-NNO2-C[H-NO2]>
and
=CH-CH2-2(NNO2)2C[-N(NO2)2]
>=CH-NNO2-CH2-NNO2-C[-N(NO2)2]>
[Edited on 27-1-2006 by Madandcrazy]
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Madandcrazy
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Some possiblity or a suggestion with the -N(NH2)2 group and the -N= binding
=N-(CH2)2-(NNO2)2C-[NO2]
>=N-CH2-NNO2-CH2-NNO2-C-[NO2]>
and
>=N-CH2-NNO2-CH2-NNO2-C-[N(NO2)2]>
Corrective to the write error in the formulas in my last post
=CH-CH2-(NNO2)2C-[NO2]
>=CH-NNO2-CH2-NNO2-C-[NO2]>
=CH-CH2-2(NNO2)2C-[N(NO2)2]
>=CH-NNO2-CH2-NNO2-C-[N(NO2)2]>
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