Tetrahedron p. 1299 - 1310 (1989)
Update date:2022-08-05
Topics:
Clewley, Robin G.
Cross, Gordon G.
Fischer, Alfred
Henderson, George N.
Nitration of p-chloro-, p-fluoro-, and p-bromo-phenol or the corresponding p-halophenyl acetates at -40 deg C and below gives the 4-halo-4-nitrocyclohexa-2,5-dienones in addition to the 4-halo-2-nitrophenols.The dienones isomerize to the nitrophenols at temperatures between -40 deg C and 0 deg C.Nitration of 4-chloro-2-methylphenol or its acetate gives both 4-chloro-2-methyl-4-nitrocyclohexa-2,5-dienone and 4-chloro-6-methyl-6-nitrocyclohexa-2,4-dienone. 4-Chloro-3-methylphenol and its acetate give 4-chloro-3-methyl-4-nitrocyclohexa-2,5-dienone.
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