UNEXPECTED REARRANGEMENT OF PHENOXYPICRAMIDE TO 1,3-DINITRO-10H-PHENOXAZINE.

The attempt to obtain phenoxypicramide from a classical nucleophilic substitution reaction using as reagents phenoxyamine and picryl chloride unexpectedly led to the formation of 1,3-dinitro-10H-phenoxazine. The possible mechanisms of formation, involving a molecular rearrangement with expelling of a nitro group, are discussed. [ABSTRACT FROM AUTHOR]