Reactions of 4-Methyl-2,6-diphenylphenol and 4-Nitro-2,6-diphenylphenol with Nitrogen Dioxide

Abstract

Reaction of 4-methyl-2,6-diphenylphenol (11a) with nitrogen dioxide in benzene solution gives the polysubstituted cyclohex-2-enones (14), (15), (16), (17) and (18) via the 4-nitro dienone (13). The reversibility of the 4-nitro dienone (13)/4-hydroxy dienone (19) conversion under these reaction conditions is demonstrated. Reaction of 4-nitro-2,6-diphenylphenol (11b) with nitrogen dioxide in benzene solution gives the C2-epimeric 2,6-dihydroxy-4,5-dinitrocyclohex-3- enones (32) and (33) via the 6-nitro-6-phenyl dienone (12b). X-ray crystal structure analyses are reported for compounds (14), (15), (16), (17), (18) and (33).