Structure and photochemistry of matrix-isolated o-phthalaldehyde

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

“…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).…”

“…We envisioned that C 60 –a well‐known radical scavenger– 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 ) . This reaction not only provides new evidence on the intermediate species involved in the photochemical transformation of 1 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 )…”

“…These enols revert back to 1 quite efficiently, and it was proposed that the formation of 2 and 3 should arise from an independent reaction pathway that involves the intermediacy of cyclic enol 10 (Figure ). The suggested ketene‐enol ( 7 ) involved in the decay of biradical 9 (from o ‐phthalaldehyde) has been further characterized by IR matrix‐isolation spectroscopy , …”