Madandcrazy
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TNCOT one step, one pot
Anyone heared of the new  compound TNCOT. (tetranitrocycloctatetrene)
It can be prepared in one step by refluxing it with concentrated H2SO4 and HNO3.
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Lambda
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Cyclooctatetraene (COT)
You mean by nitrating Cyclooctatetraene (COT) with mixed acid.
Cyclooctatetraene looks similar to benzene, except; not having 6 but 8 cyclic carbon atoms. Apparently Cyclooctatetraene is not aromatic because it is
nonplanar.
http://chemweb.stanford.edu/fall2004/chem131/Handouts/week2....
Maybe more clarity concerninng the nitration of Cyclooctatetraene can be found in this artical:
M. Tanaka,* E. Muro, H. Ando, Q. Xu, M. Fujiwara, Y. Souma, Y. Yamaguchi, “NO2+ Nitration Mechanism of Aromatic Compounds: Electrophilic vs
Charge-Transfer Process”, J. Org. Chem., 65, 2972-2978 (2000)
Other articals by the same author are:
Shu Zhang, Qiang Xu,* Jie Sun, and Jiabi Chen,* “Remarkable Reactions of Cyclooctatetraene-coordinated Diiron Bridging Carbyne Complexes with Amine
Compounds. Nucleophilic Addition to and Breaking of Cyclooctatetraene Ring”, Chem. Eur. J., 9, 5111-5122（2003).
Lei Zhang, Shu Zhang, Qiang Xu,* Jie Sun, and Jiabi Chen*, “Cyclooctatetraene (COT)-Coordinated Diiron Carbene Complexes and Their Remarkable
Thermolysis Reactions”, Organometallics, 24, 933-944 (2005).
Check out the structure of Cyclooctatetraene (allso seen in top (first) link: week2.pdf):
http://www.usm.maine.edu/~newton/Chy251_253/Homeworks/Chy253...
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Madandcrazy
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Thanks for the informations Lambda.
I mean the Cyclooctatetraene (COT), it was a simple write error by me.
The PDF dosen`t walk for me. 
I think of interest too is the syntheses of
COT by cycloaddition with easy available chemicals.
[Edited on 29-6-2005 by Madandcrazy]
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my nootloss
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"If you train it more you might be able to get it to walk.  " yes, yes, very
funny  please don't clog the board up... cheers
[Edited on 27-3-2006 by Ramiel]
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Madandcrazy
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Interested to the topic is the sysnthesis of [cyclooctatetraene by more than one step, chlororethylene, chlororamin or a acetate...] or cylooctane,
contingently by 1-chlorooctanoic acid or n-octane.
More maybe, when started with 1,3,5,7,-tetrachlorocyclooctane (TCCOT, by chlorination) and the 1,3,5,7,-tetrachlorocyclooctane is than converted to
1,3,5,7,-tetraaminocyclooctane. Most interested is when the 1,3,5,7,-tetraaminocyclooctane is reacted with 1,5-dichlorodiethylketone and the material
is than nitrated like TNGU to a tetrazine or a octanitrate which have extra four nitro groups (-CHNO2-).
I don`t know the idea walking fine and the 1,3-dichlorodiethylketone is not crossreacted with the chloro atoms of 1,3,5,7,-tetrachlorocyclooctane?
Eventually interested for this the topic of substitution with different halogens.
[Edited on 26-3-2006 by Madandcrazy]
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PHILOU Zrealone
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I think dat because cyclooctatetr(a)ene is non aromatic it wil behave like conjugated alcenes upon contact with H2SO4 and HNO3 ...
Result wil thus be partial addition of water, of HNO3, of N2O4, and resulting nitratation/oxydation products...
I thus think dat the compound is of interest because of its weird shape but polynitrocompounds must be reached via other means than direct contact
with HNO3/H2SO4.
There are other ways but I would think to tetramerisation of O2N-CH2-CH=O with the help of a metalic catalyst cation that would favourise octaring vs
hexaring....you of course know the natural favourised cyloaddition compound is the trimeric sym-TNB (1.3.5 Trinitrobenzene)...
As a side note O=CH-CHNO2-CH=O also turns spontaneously into TNB when left in water or in basic media.
 
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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Madandcrazy
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Tanks for the detailed chemical info and the catalysation. A good example was NONA.
I mean interested is maybe the nitration of mixed components (-NNO2 and -CHNO2-), you would continuing nitrating a azine component with H2SO4 and
HNO3, do it decompose ? The -CH3- group should be nitrated before the amin is substituted ?
All known is a azine decompose in saturated NaOH solution.
Exuse me for my the error in the post, the component with the dichlorodiethylketone should have 12 nitro groups.
Maybe a cycloaddition to a nitrocyclooctane... is possible when the 1-chlorooctanoic acid is threated with a mixture of a acetate and nitration
mixture.
I think in theorie most interested is when for instance
a caged starting material was synthesized similar to urotropin what is available and which have a cage ring with four nitrogen atoms. Is it possible
to when the Octogen is reacted with carbon tetrachloride, a amide or tetrachlorotetramethylcarbon to this unkown material.
[Edited on 2-4-2006 by Madandcrazy]
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