THE REARRANGEMENT OF ALLOXAN AND ITS DERIVATIVES (thesis)
C/sup 14/ was used to follow the course of the rearrangement of alloxan, together with tts derivatives, from a 6membered to 5-membered ring. Alloxan-5-C/ sup 14/ was rearranged to alloxanic acid under several different conditions of pH. Chromic acid oxidation of the alloxanic acid so produced yielded parabanic acid which contained all of the radioactivity associated with the starting alloxan. Thus, a nitrogen-carbon bond rather than a carbon-carbon bond was obviously broken, in disagreement with previous theory concerning the mechanism of the rearrangement. Confirmatron of these results was obtained upon rearrangement of alloxan-4-C/sup 14/, for the resultant parabanic acid contained one-half the radioactivity of its precursors. Substitution of the various R groups on the nitrogens did not alter the result. In several unsymmetrically substituted alloxans, it was possible to determine the relative migratory aptitudes of the nitrogen-carbon bonds contained in the alloxan molecules. (auth)
- Research Organization:
- Oak Ridge National Lab., Tenn.
- DOE Contract Number:
- W-7405-ENG-26
- NSA Number:
- NSA-16-022165
- OSTI ID:
- 4837882
- Report Number(s):
- TID-16048
- Country of Publication:
- United States
- Language:
- English
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