Radical isomerization via intramolecular ipso substitution of aryl ethers: Aryl translocation from oxygen to carbon

Article abstract of DOI:10.1016/S0040-4039(00)77609-X

Bromopropyl aryl ethers an converted to 3-arylpropanols under standard radical generating conditions in the presence of tributylstannane and AIBN. This rearrangement involves intramolecular ipso attack of the alkyl radicals which generates spiro cyclohexadienyl radical intermediates.