2006
DOI: 10.1021/jp055878x
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Photoinduced Decarboxylative Benzylation of Phthalimide Triplets with Phenyl Acetates:  a Mechanistic Study

Abstract: The photodecarboxylative benzylation of N-alkyl, N-arylalkyl, and N-aryl phthalimides with arylacetic acids in aqueous solution proceeds via electron transfer from the arylalkanoate to the excited triplet state of the phthalimide, either formed directly or upon sensitization with acetone. The rate constant for triplet quenching of N-methylphthalimide is k(q) < 10(7) M(-1) s(-1) for 2-phenylacetic acid and k(q) = (1-3) x 10(9) M(-1) s(-1) for its mono-, di- and trimethoxy-substituted derivatives, suggesting a c… Show more

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Cited by 54 publications
(43 citation statements)
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“…For a photochemical study of the title compound, see: Warzecha, Gö rner et al (2006). For related compounds, see: Lü et al (2006); Warzecha et al (2006a); Chen et al (2006).…”
Section: Related Literaturementioning
confidence: 99%
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“…For a photochemical study of the title compound, see: Warzecha, Gö rner et al (2006). For related compounds, see: Lü et al (2006); Warzecha et al (2006a); Chen et al (2006).…”
Section: Related Literaturementioning
confidence: 99%
“…
Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.034; wR factor = 0.087; data-to-parameter ratio = 13.9.The title compound [systematic name: 2-(4-methoxybenzyl)-isoindoline-1,3-dione], C 16 H 13 NO 3 , represents a triclinic polymorph of the previously reported monoclinic form [Warzecha et al (2006). Acta Cryst.
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mentioning
confidence: 96%
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“…In recent years, we and others have intensively investigated the non‐catalytic intermolecular photoaddition of alkyl carboxylates to phthalimides . The mechanistic details were elucidated for the chromophore component (triplet state and radical anion detection) by static and time‐resolved spectroscopic methods . These intermolecular photoinduced electron transfer reactions lead to an interesting class of products, 3‐hydroxyisoindolinones, that can be further dehydrated to 3‐methylene derivatives or deoxygenated to biologically relevant isoindolinones .…”
Section: Introductionmentioning
confidence: 99%
“…N-Alkylated phthalimides typically absorb in the 295 nm region with extinction coefficients around 10 3 . The quantum yields for intersystem crossing Ф ISC significantly change with the substitution on the imide nitrogen, e.g., Ф ISC = 0.5 for N -isobutylphthalimide and Ф ISC < 0.01 for N -arylphthalimides [1]. If necessary, the population of the triplet state is also possible by sensitization, e.g., with triplet sensitizers such as acetone or benzophenone.…”
Section: Introductionmentioning
confidence: 99%