Photochemistry of matrix-isolated o-phthalaldehyde

Photochemical Reaction of o‐Phthalaldehyde with Fullerene C60: The Stimulus for the Phthalide Additions to C60

“…We envisioned that C 60 -a well-known radical scavenger- [8] would react promptly with the free-radical intermediates formed upon irradiation of o-phthalaldehyde, especially with acyl radical 5 as shown in a previous study that regards the prompt reactivity of C 60 towards acyl radicals (Figure 1). [9] This reaction not only provides new evidence on the intermediate species involved in the photochemical transformation of 1 [1][2][3][4][5][6][7] but, at the same time, also provide a novel synthetic route for the functionalization of [60]fullerene and access to new nanostructures with potentially interesting properties.…”

“…The photochemical isomerization of o-phthalaldehyde (1) to phthalide (2) and an isomeric mixture of the corresponding dimers (3), has been the subject of several studies (Scheme 1). [1][2][3][4][5][6][7] Scheme 1. Photochemical transformation of o-phthalaldehyde (1) to phthalide (2) and its dimer (3).…”

“…The suggested ketene-enol (7) involved in the decay of biradical 9 (from o-phthalaldehyde) has been further characterized by IR matrix-isolation spectroscopy. [5,6] The aim of the present study was to investigate the photochemical reaction of 1 in the presence of [60]fullerene. We envisioned that C 60 -a well-known radical scavenger- [8] would react promptly with the free-radical intermediates formed upon irradiation of o-phthalaldehyde, especially with acyl radical 5 as shown in a previous study that regards the prompt reactivity of C 60 towards acyl radicals (Figure 1).…”

“…The photochemical isomerization of o ‐phthalaldehyde ( 1 ) to phthalide ( 2 ) and an isomeric mixture of the corresponding dimers ( 3 ), has been the subject of several studies (Scheme )…”

The photoformation of a phthalide: a ketene intermediate traced by FSRS

“…15 As the initial process of this reaction, the computations predict a non-adiabatic hydrogen transfer resulting in a ketene. 16 However, this experiment gave neither information on the time scale of the formation nor on its yield. 16 However, this experiment gave neither information on the time scale of the formation nor on its yield.…”