Tetrazenes derivatives

The product of reaction between / -tosylazide and substituted 5-aminopyrazoles was observed to be dependent on the extent of the substitution on the heterocyclic ring. Thus l,3-diphenyl-5-aminopyrazole (88) reacted with tosylazide in ethanol, in the presence of NEt3, to afford the pyrazolotriazole (89) (Equation (12)). On the other hand, the 3-phenyl substituted pyrazole (90) reacted under the same conditions to furnish the tetrazene derivative (91) (Equation (13)) <85MI 705-01). 

Mercury(ll) fulminate - Used since the early 1800s in percussion caps for black powder shooting, this primary explosive is highly sensitive to friction and shock. Thus it is used to trigger secondary, but more powerful explosives. Although potassium chlorate is sometimes used in its place, the mercury(ll) fulminate is less corrosive, but may weaken with time. Today it is usually replaced with materials that are non-corrosive, less toxic and more stable over time lead azide, lead slyphnate and tetrazene derivatives. It also causes brass to become brittle a concern for reloaders. 

Expls may be classified both from the chemical point of view and according to their uses. From the chemical viewpoint we distinguish between chemical individual substances and mixts. The former are divided into (1) nitro compds, (2) nitric esters, (3) nitramines, (4) derivatives of chloric and perchloric acids, (5) azides, and (6) various compds capable of pro-during an expln, for example fulminates, acetyl-ides, nitrogen rich compds such as tetrazene, peroxides and ozonides, etc... 

Compounds with the classical nonsystematic name diazoamino compound (R-N2NRiR2) and their (logical) derivatives with two or more adjacent nitrogen atoms are considered as substitution products of triazene (NH2 — N=NH), 1-tetrazene, etc. (Rule 942.1). Simple examples are 3-methyltriazene (CH3-NH-N = NH) and 3-methyl-l-tetrazene [NH2-N(CH3)-N = NH]. The classical name is retained only for compounds containing the same group R at each end of an - N=N - NH - group (Rule C-942.2), e. g., A-methyldiazoaminobenzene,... 

On reduction, nitroguanidine is converted first into nitrosoguanidine and then into aminoguanidine i.e. guanylhydrazine. The latter is used for the manufacture of tetrazene (p. 206), and in organic chemistry to form crystalline derivatives from aldehydes and ketones, just as semicarbazide forms semicarbazones. 

Wohl Schiff (Ref 2) to compds of the general formula R1. N N.NRtt.NH2i where R is an H or alkyl R11 is an aryl group. These compds may be considered as derivatives of hypothetical "tetrazene , HN N.NH.NH2> and they resemble the compd... 

Part I. Transition metal derivatives of triazenes, tetrazenes, tetrazadienes, and pentazadienes. Adu. Inorg. Chem. Radiochem. 30, 1 (1986). 

Chemical analysis of expl reaction products has been performed utilizing spectroscopic methods. A study of the thermal decompn of Tetrazene at 90° has demonstrated that substantially complete conversion to 5-aminotetra-zoie is effected (Ref 69). Spectroscopic evidence has indicated that this product is derived from both the side chain (guanyl azide) and the Tetrazole ring. Utilizing the unique-to-mercury absorption line at 2536.5a, mercury (II) concn... 

Tetrazene (Tetrazen in Ger) is a collective name for derivatives of compds contg 4 nitrogens in a straight chain, such as Tetrazene (1),... 

R. Bird A.J. Power. Thermal Decomposition of Tetrazene at 90°C , MRL-R-710, Australia (1978) [The authors report that Tetrazene is converted into 5-aminotetrazole in less than three days at 90°, thus losing its stab sensy property. Spectroscopic evidence indicates that the 5-aminotetrazole is derived from both the side chain (via guanyl azide) and the Tetrazole ring] 24) G.B. Franklin C.F. Parrish, Radiation Polymerized Priming Compositions , USP 4056416 (1977) CA 88, 52661 (1978) [The inventors claim that extrudable primers with good percussion sensy are prepd from Tetrazene 3.9—4.1, n-Pb Styphnate 32—42,... 

Many attempts were made to synthesize the diazaazulene derivative 4,7-diphenyl-5,6-diazaazulene 34. A directed synthesis of diazaazulene 34 by [6+4] cycloaddition of fulvenes with 1,2,4,5-tetrazenes when attempted with 2-cyclopenta-dienyliden-l,3-dioxolane led to the formation of cyclopcnta[z/ pyridazines via a [4+2] cycloaddition pathway <2001TH1>. 

Intramolecular cyclizations of alkenylaminyl radicals produced from tetrazenes have been reported. The regioselectivity of cyclizations of aminyl radicals derived from N-3-butenyltetrazene (1), A-4-pentenyl tetrazene (2), and JV-5-hexenyl tetrazene (3) have been studied (78MI1). The position of the alkene moiety is important because other reaction pathways can compete with cyclization. 

However, the reactivity of 5-hydrazinotetrazole 422 in reactions typical of a hydrazine is poorly documented. An example of the reactivity of some derivatives of 5-hydrazinotetrazole (e.g., 405) in the synthesis of high-nitrogen tetrazole derivatives, such as l,4-bis-[l-methyltetrazol-5-yl]-l,4-dimethyl-2-tetrazene 47, is shown in Scheme 48 <2004MI325>. 

Catenated Nitrogen Ligands Part I. Transition Metal Derivatives of Triazenes, Tetrazenes,... 

CATENATED NITROGEN LIGANDS PART 1. TRANSITION METAL DERIVATIVES OF TRIAZENES, TETRAZENES, TETRAZADIENES, AND PENTAZADIENES... 

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