A THERMALLY-INDUCED RADICAL REARRANGEMENT OF 2-ARYLMETHOXYTROPONES TO 3- AND 5-ARYLMETHYLTROPOLONES

Article abstract of DOI:10.1246/cl.1981.73

2-Arylmethoxytropones, i.e., 2-benzyloxytropone, 2-(p-tolylmethoxy)tropone, 2-(4-bromophenylmethoxy)tropone, 2-(4-chlorophenylmethoxy)tropone, 2-(4-methoxyphenylmethoxy)tropone, and 2-(1-naphthylmethoxy)tropone, rearranged upon heating to the 3- and 5-arylmethyltropolones via the radical intermediates.Similarly, 5-bromo-2-(p-tolylmethoxy)tropone gave 5-bromo-3-(p-tolylmethyl)tropolone.