Proximity effects in diaryl derivatives. Part V. Syntheses of 2,7-and 2,8-dichlorophenoxazine derivatives. Smiles rearrangements activated only by halogen substituents
- 1 January 1966
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 266-269
- https://doi.org/10.1039/j29660000266
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.Keywords
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