Photochemistry of o-phthalaldehyde

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Abstract
U.v.-irradiation of o-phthalaldehyde leads to the formation of phthalide and dimeric products in varying yields and ratios depending on the solvent and reagent concentration. Laser flash photolysis studies show that the photochemistry of o-phthalaldehyde involves the intermediacy of a 1,4-biradical produced by intramolecular hydrogen transfer, and with a lifetime of 1.6 µs. Two triplet states are the precursors of this biradical; they have lifetimes of 6 and 36 ns and are assigned to different rotational conformers. The triplet reaction path is not responsible for product formation; these arise via a parallel reaction path, apparently involving the singlet state.

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