ChemInform Abstract: Novel Base-Promoted Rearrangement of 2-(4-Cyano-, 2-Nitro-, and 4-Nitrobenzyloxy)tropones and 2-(2-Oxo-2-phenethyloxy)tropone to 2-((4-Cyano-, 2-Nitro-, and 4-Nitrophenyl)hydroxymethyl)tropones and 2-(1-Hydroxy-2-oxo-2-phenethyl)tropone.

ChemInform Abstract

Reaction of the tropolonate (I) with the benzylhalogenides (II) or (VI) affords the benzyloxytropones (III) as main products. Thermolysis of (III) affords the benzyltropolones (IV), while base-catalyzed rearrangement of (III) yields the ((phenyl)hydroxymethyl)tropones (V), which are oxidized to the ketones (VII). Reaction of (I) and phenacyl bromide (VIII) affords the rearrangement product (X) asmain component.