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Encyclopedia Britannica



ISOXAZOLES

This article appears in Volume V14, Page 885 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: INV-JED
ISOXAZOLES , monazole chemical compounds corresponding to furfurane, in which the -CH
group
  adjacent to the oxygen
atom is replaced by a nitrogen atom, and therefore they contain H C = N
the
ring
 
system
  >O They may be prepared
HC =CH
by the elimination of water from the monoximes of 0-
diketones
 , 0-ketone aldehydes or oxymethylene
ketones
  (L. Claisen, Ber., 1891, 24, p. 3906), the general reaction proceeding according to the equation
RCOCH2COR+H2N .OH =2H20+RC = N
HC=C-R
W. Dunstan and T. S. Dymond (Jour. Chem. Soc., 1891, 49, p. 410) have also prepared isoxazoles by the action of alkalis on nitroparaffins, but have not been able to obtain the
parent
  substance. Those isoxazoles in which the carbon atom adjacent to nitrogen is substituted are
stable
  compounds, but if this is not the
case
 , rearrangement of the molecule takes
place
  and nitriles are formed. The isoxazoles are feebly basic.
The isoxazolones are the keto derivatives of the as yet unknown 'dihydroisoxazole, and are compounds of strongly acid nature, decomposing the carbonates of the alkaline earth metals and forming salts with metals and with
ammonia
 . Their constitution is not yet definitely fixed and they may be regarded as derived from one of the three types


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