New tetrahydro-1,2,4,5-tetrazinan-3-ones and oxoverdazyl free radicals

A series of tetrahydro-1,2,4,5-tetrazinan-3-ones have been prepared by the reaction of carbonic acid bis (1-methylhydrazide) with aromatic aldehydes. These were oxidised to oxoverdazyl free radicals and used immediately for ESR spectroscopy studies that indicate that the unpaired electron is delocalised over the verdazyl ring. The ESR spectra can be very well simulated considering hyperfine couplings with the four nitrogen atoms of the verdazyl ring and the six hydrogen atoms of the two methyl groups bonded to it.