Nick F - 15-9-2002 at 08:15
These are just a few ideas I've had recently (I've been reading my new book on heterocyclic chemistry and it's been giving me ideas), I thought I'd
post them to see what you thought, and hopefully get some interesting discussions going:
Diazotisation of melamine with NaNO2 and HNO3:
(NC(NH2))3 + 6 HNO3 + 3 NaNO2 --> (NC(N2+)(NO3-))3 + 3 NaNO3 + 6 H2O
And diazotisation of 5-aminotetrazole with NaNO2 and HNO3:
C(NH2)N4H + 2 HNO3 + NaNO2 --> C(N2+)(NO3-)N4H + NaNO3 + 2 H2O
("Heterocyclic Chemistry, Fourth Edition" by Joule and Mills states that C(N2+)(Cl-)N4H can lose HCl to form N2CN4, any ideas on how to achieve this?)
React ethyne with NaN3 in a suitable solvent, then add dilute HCl to form 1,2,3-triazole:
C2H2 + NaN3 + HCl --> C2H2N3H + NaCl,
then react this with Br2 or I2, then with 2 NaNO2 to form 4,5-dinitro-1,2,3-triazole, -C(NO2)=N-(NH)-N=C(NO2)- (join the ends up).
I'm particularly interested in the safety of the diazo- 5-ATZ compound, and of the last procedure, because they're the ones I'm thinking of trying...
Danger ahead...
Polverone - 16-9-2002 at 11:30
Diazotetrazole is extremely sensitive, unstable even in cold aqueous solution. This is all I was able to find with an hour of searching, now that I
have to go to the library and flip through journals to find info older than 1996. I have found a reference to a large review article, "The Chemistry
of the Tetrazoles," Chemical Reviews, 1947, which includes information on their explosive derivatives. Perhaps you could obtain this article through
an interlibrary loan or the like? I might try finding out how to obtain this article myself, now that I can't view the ACS archives.
Such a brave soul......
PrimoPyro - 16-9-2002 at 18:14
If you are this brave, perhaps you would be interested in diazotizing melamine with 3NaNO2 + 6HCN, forming the cyanide diazo salt. [crazy]
I dont know from first hand experience, but Ive heard that cyano groups house a shitload of energy...........cyanogen burns in O2 at something around
5000K I heard once. 
PrimoPyro
Nick F - 17-9-2002 at 09:27
Strange that diazotetrazole is that bad, I've got a few g of dry ditetrazolyltriazine (I found it mentioned in COPAE, and just had to make it) here,
it's c. a week old and shows no sign of any changes. It's been at room temp., at ambient light levels. It is my intention to keep it like this for a
few months and see if anything happens to it. At the moment it's a very light salmon pink colour, I've recrystalised it twice from water and washed it
with isopropanol.
That review article could be very interesting, I'll try and get my hands on it...
The CN- salt wouldn't be as good I don't think, no O present and 6 C's. But with HN3... 
Nick F - 24-11-2002 at 14:26
For anyone that's interested, the sample of ditetrazolyltriazine still looks and behaves exactly as it did when freshly made. I have found that it is
slightly hygroscopic, the granules absorbing moisture from the air but not enough for any liquid to be present. Although it is quite a damp room.
I tried another experiment today, I was hoping to oxidise aminotetrazole to form ditetrazolyldiazine with NaOCl (2 N4HC-NH2 + 2 NaOCl -->
N4HC-N=N-CN4H + 2 NaCl), but unsurprisingly I just ended up with a load of bubbles and no useful product 
Also I've been trying to find out if it's possible to open up the ring in aminotetrazole to form guanyl azide, but have found very, very little
information on the reactions of aminotetrazole or other tetrazoles in general. All I found out was that in acidic or weakly alkaline solutions, guanyl
azide can form aminotetrazole (although it can be boiled in pure water without change).
Regarding the synthesis of 1,2,3-triazole, I think I will start experimenting a bit tomorrow. It's been said that the cycloaddition of HCN and C2H2 to
form pyridine is catalysed by UV (in aqueous solution), as the reaction I'm interested in is a little bit similar do you think the same method could
be used? Or would UV cause too much decomposition?
There was a catalyst mentioned for the trimerisation of acetylene too, Zn(CN)2 was it? Do you think a similar substance might work here?
Android - 8-1-2003 at 02:52
A guy called Shevlin (among others) has made diazotetrazole, and decomposed it to carbon....and very reactive carbon at that. Apparently it's not even
stable at -70 degrees in ether!!
Its use and decomposition is pretty well documented.
PHILOU Zrealone - 18-3-2003 at 08:19
Diazotation of melamine might work but care must be taken owing to the extreme sensitivity of monodiazotation; here you are attempting a
tridiazotation...some diazotate explode fearcely when in solution or when damp wet;
Actually one of the worst is the bromide, sulfate and one of the powerfullest is perchlorate!
HCN won't make cyanide salt in NaNO2 media; HCN is a weaker acid than HNO2 thus it can't displace it from its salts; no diazotation will
happen!
Anyway the trichloride may enter an exchange resin to substitute for tricyanide but I really think the compoud is so sensitive it will decompose under
standing!