Irradiation of 4-phenylchroman-3-one in ben-zene gave 2-phenylchroman-3-one as the only photo-product; the mechanism involves β-scission and recoupling of the diradical produced through the aromatic ring to give a transient spirocyclohexadienone which gives the product by a 1,3-sigmatropic shift.
A. Padwa and A. Au, J. Chem. Soc., Chem. Commun., 1975, 58 DOI: 10.1039/C39750000058
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