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Encyclopedia Britannica



FURAZANES (furoa.a'diazoles)

This article appears in Volume V11, Page 357 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: FRA-GAE
FURAZANES (furoa.a'diazoles) , organic compounds obtained by
heating
  the glyoximes (dioximes of ortho-
diketones
 ) with alkalis or
ammonia
 . Dimethylfurazane is prepared by
heating
  dimethylglyoxime with excess of
ammonia
  for six
hours
  at 165 C. (L. Wolff, Ber., 1895, 28, p. 70). It is a liquid (at
ordinary
  temperature) which boils at 156 C. (744 mm.). Potassium permanganate oxidizes it first to methylfurazanecarboxylic acid and then to furazanedicarboxylic acid. Methylethylfurazane and diphenylfurazane are also known. By warming oxyfurazane acetic acid with excess of potassium permanganate to roo C. oxyfurazanecarboxylic acid is obtained (A. Hantzsch and J. Urbahn, Ber., 1895, 28, p. 764). It crystallizes in prisms, which melt at 175 C. Furazanecarboxylic acid is prepared by the action of a large excess of potassium permanganate on a hot solution of furazanepropionic acid. It melts at 107 C., and dissolves in
caustic
  soda, with a deep yellow colour and formation of nitrosocyanacetic acid (L. Wolff and P. F. Ganz, Ber., 1891, 24, p. 1167). Furoxane is an
oxide
  of furazane, considered by H. Wieland to be identical with glyoxime peroxide;
Kekule
 's dibromnitroacetonitrile is dibromfuroxane.
The formulae of the compounds above mentioned are: HC: N CH3C: N>0 HC : N>O
H:N CHa C: N HO2CC: N
Furazane. Dimethyl- Furazane-
furazane. carboxylic acid.


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