Abstract
Syntheses of N-benzyl-2,7-dichlorophenoxazine and 2,8-dichlorophenoxazine show that the dichlorophenoxazine obtained2 by reduction of 4,4′-dichloro-2,2′-dinitrodiphenyl ether with lithium aluminium hydride is the 2,8-isomer. The formation of this compound, therefore, does not involve a Smiles rearrangement.Reaction of 2′-benzylamino-2,4′,5-trichlorodiphenyl ether with potassium carbonate in dimethylformamide results in Smiles rearrangement to N-benzyl-2,8-dichlorophenoxazine, although the ring subject to nucleophilic attack is activated only by halogen substituents.
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