Heterocyclic bases perchlorates

The very attractive characteristics of the perchlorates of heterocyclic bases were discovered with pyridine perchlorate which was first prepared by Cordier [35] and described by Arndt and Nachtwey [36]. The explosive properties of pyridine perchlorate were described by Muraour and Wohlgemuth [37]. 

Explosive properties of perchlorates of heterocyclic bases (T. Urbanski and Kowalski [34]>... 

The reaction of aminoguanidine bicarbonate (84) with sodium nitrite in the presence of excess acetic acid produces 1,3-ditetrazolyltriazine (89), another nitrogen-rich heterocycle (C2H3N11 = 85 % N) which readily forms explosive metal salts. The reaction of aminoguanidine bicarbonate (84) with sodium nitrite in the presence of mineral acid yields guanyl azide (90), of which, the perchlorate and picrate salts are primary explosives. Guanyl azide (90) reacts with sodium hydroxide to form sodium azide, whereas reaction with weak base or acid forms 5-aminotetrazole. ... 

On condensation of peri-hydroxynaphthaldehydes with the Fischer base (82KGS1501) or with 1,3,3-trimethylisobenzofurylium perchlorate (86DOK639), 2-substituted heterocyclic 2//-naphtho[6c]furan derivatives... 

Both acid and base catalysis have been used extensively to catalyze exchange in aromatic, and to a lesser extent, heterocyclic molecules. In acid exchange, the most widely used catalysts are sulfuric acid,122,129, 131 phosphoric acid,132 trifluoroacetic acid5133 perchloric acid,134 aluminum chloride,135 and the phosphoric acid-boron trifluoride complex.132 These reactions constitute the simplest electrophilic substitution. The mechanism for such substitution in benzenoid compounds is now comparatively well understood 122 however, the problem of heteroaromatic electrophilic substitution is still being clarified and has led to renewed interest in acid-catalyzed exchange in heterocyclic compounds.122... 

Hetisine-13-0-acetate (3) is a new base isolated in very small amounts (such that chemical studies are precluded) from Delphinium nuttallianum Printz. Its structure has been settled in part by X-ray diffraction analysis of its perchlorate the absolute configuration remains to be determined (M. H. Benn et al., Heterocycles, 1986, 1605). Spirasines... 

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