Some Rearrangements of 2,4,6-Tri-t-butyl-4-nitrocyclohexa-2,5-dienone

Abstract

Rearrangement of 2,4,6-tri-t-butyl-4-nitrocyclohexa-2,5-den (20) in benzene gives the 4-hydroxy dienone (21) and the mono-de-t- butylated 1,2-benzoquinone (22). The rearrangement is not affected by the addition of mesitylene , but the phenol-coupling product (26) is formed in the presence of p-cresol, and the nitromethyl phenol (31) is formed when the nitro dienone (20) rearranges in the presence of 2,4,6- trimethylphenol (29). The rearrangements of the nitro dienone (20) in methanol are described.