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1462 J.Org. Chem. 1982,47, 1462-1468 products of the oxidation, conditions under which dimer
 

Summary: 1462 J.Org. Chem. 1982,47, 1462-1468
products of the oxidation, conditions under which dimer
7 dissociates very little. Workup of the reaction gives solid
1 contaminated with dimer 7. When 1 is purified by
sublimation it dissociates at the higher temperatures
(40-50 "C) into 2 which sublimes along with 1. The azo
compound 1 is so soluble in organic solvents it must be
crystallized at low temperatures, and as a result the higher
molecular weight (and presumably less soluble) dimer
cocrystallizeswith the azo compound. When this mixture
of 1and 7 is in solution at room temperature and above,
7 dissociates into 2, which slowly changes to the thermo-
dynamically more stable final radical 6. This radical is
itself in equilibrium with dimer 8 as shown by the en-
hancement of the ESR signalas the temperature is raised.
In two cases, samples of triazolinediones were obtained
which were free of detectable radical. The first was a
degassed ESR sample of la in ether that stood at room
temperature for 18h. This sample on warming to 55 O C
gave the final radical 6. Apparently the dissociation of the

  

Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology

 

Collections: Chemistry