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Encyclopedia Britannica



TETRAZOLES

This article appears in Volume V26, Page 671 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: TAV-THE
TETRAZOLES , in organic
chemistry
 , a
group
  of heterocyclic compounds, capable of existing in two isomeric
series
  (formulae 1 and 2), although the methods of preparation do not always permit discrimination between the possible isomers. They are prepared by the action of nitrous acid on cyanamidrazone (dicyanophenylhydrazine) and
hydrolysis
  of the resulting nitrile, from which J. A. Bladin by elimination of the phenyl
group
  (by nitration, reduction, &c.) and of carbon dioxide obtained free tetrazole, CH4N2; from amidines by the action of nitrous acid, followed by the reduction of the intermediately formed dioxytetrazotic acids with sodium amalgam; from amidoguanidine by diazotization, the diazonium nitrate. on treatment with acetates or
carbonates
  yielding aminotetrazole (J. Thiele, Ann., 1892, 270, p. 1); from the action of nitrous acid on phenylthiosemicarbazide; and by the action of arylazoimides on aldehyde hydrazones (O. Dimroth, Ber., 1907, 40, p. 2402). The tetrazoles behave as strong monobasic acids, and are exceedingly
stable
 . A
series
  of tetrazolium bases (
formula
  3) have been obtained by H. V. Pechmann (Ber., 1894, 27, p. 2020) starting from formazyl compounds (
formula
  4), which are oxidized by means of amyl nitrite and hydrochloric acid. They are strong bases, which in aqueous solution absorb carbon dioxide readily. The free bases have not been isolated, but their salts are well-crystallized solids.
/N:N l/NNH /N:CH RHN-N:CH
HN\N:CH or N\N:CH RN\N:N RN:N
HO
(1) , (2) . (3) , (4).


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