Tetrahedron

Formation of 4-Halo-4-nitrocyclohexa-2, 5-dienones on Nitration of p-Halophenols and p-Halophenyl Acetates

RG Clewley, GG Cross, A Fischer, GN Henderson

文献索引：Clewley, Robin G.; Cross, Gordon G.; Fischer, Alfred; Henderson, George N. Tetrahedron, 1989 , vol. 45, # 5 p. 1299 - 1310

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被引用次数: 13

摘要

Nitration of p-chloro-, p-fluoro-, and p-bromo-phenol or the corresponding p-halophenyl acetates at t-40° 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° C and 0° 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, ...