Some rearrangements of 2,3,5,6-Tetrachloro-4-methyl-4-nitrocyclohexa-2,5-dienone and 3,5-Dibromo-2,4,6-trimethyl-4-nitrocyclohexa-2,5-dienone

Abstract

The rearrangements of the 4-nitrocyclohexa-2,5-dienones (3) and (4) in (D)chloroform and benzene are reported, and the rearrangement mechanisms discussed. In the presence of added phenols (18) and (20), nitromethylphenols (19) and (21) are formed in addition to the normal rearrangement products. The mechanistic implications of this observation are discussed.