It was reported in a previous paper that azoxybenzene undergoes the wallach rearrangement with trichloroacetic acid catalyst in boiling acetic anhydride. This method was applied to various azoxy compounds. (1) 2, 2- and 4, 4- Dimethyl azoxybenzenes gave 4- and 2-hydroxyazo compounds respectively in good yields. (2) The yield of
o-hydroxyazo compounds was higher than that of
p-hydroxyazo compounds in both cases of α-
p-methyl and α-
p-methoxy azoxybenzene. (3) No reaction occurred with β-
p-nitro azoxybenzene (4) Dichloro and monochloroacetic acids were found to be also effective for the rearrangement of 2, 2'-dimethyl azoxybenzene, although in less yield.
View full abstract