THE ENCYCLOPÆDIA BRITANNICA

A DICTIONARY OF ARTS, SCIENCES, LITERATURE AND GENERAL INFORMATION

ELEVENTH EDITION 1911

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AZOXIMES (furo [a.b.] diazoles), a class of organic compounds which contain the ring system
HC = N 
 N = CH
\
/
O.

They may be prepared by converting nitriles into amidoximes by the action of hydroxylamine, the amidoximes so formed being then acylated by acid chlorides or anhydrides. From these acyl derivatives the elements of water are removed, either by simple heating or by boiling their aqueous solution; this elimination is accompanied by the formation of the azoxime ring. Thus

C6H5CN NH2OH
———>
 
C6H5·C//
\
N·OH
 
NH2
boil with
———>
propionic anhydride
[C6H5C//
\
N·O·COC2H5
 
NH2
]——> C6H5·C//
\
N·O
 
N
\
//
C·C2H5

[v.03 p.0086]

Azoximes can also be produced from α-benzil dioxime by the "Beckmann" change. Most of the azoximes are very volatile substances, sublime readily, and are easily soluble in water, alcohol and benzene.

For detailed descriptions, see F. Tiemann (Ber., 1885, 18, p. 1059), O. Schulz (Ber., 1885, 18, pp. 1084, 2459), and G. Müller (Ber., 1886, 19, p. 1492); also Annual Reports of the Chemical Society).


Transcriber's note: A few typographical errors have been corrected. They appear in the text like this, and the explanation will appear when the mouse pointer is moved over the marked passage. Sections in Greek will yield a transliteration when the pointer is moved over them, and words using diacritic characters in the Latin Extended Additional block, which may not display in some fonts or browsers, will display an unaccented version.

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