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Oksdath-Mansilla G, Heredia AA, Argüello JE, et al. Photochemistry of N-(selenoalkyl)-phthalimides. Formation of N, Se-heterocyclic systems. Photochem Photobiol Sci. 2015;14(4):726-36doi: 10.1039/c4pp00452c.
Oksdath-Mansilla, G., Heredia, A. A., Argüello, J. E., & Peñéñory, A. B. (2015). Photochemistry of N-(selenoalkyl)-phthalimides. Formation of N, Se-heterocyclic systems. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 14(4), 726-36. https://doi.org/10.1039/c4pp00452c
Oksdath-Mansilla, Gabriela, et al. "Photochemistry of N-(selenoalkyl)-phthalimides. Formation of N, Se-heterocyclic systems." Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology vol. 14,4 (2015): 726-36. doi: https://doi.org/10.1039/c4pp00452c
Oksdath-Mansilla G, Heredia AA, Argüello JE, Peñéñory AB. Photochemistry of N-(selenoalkyl)-phthalimides. Formation of N, Se-heterocyclic systems. Photochem Photobiol Sci. 2015 Apr;14(4):726-36. doi: 10.1039/c4pp00452c. PMID: 25597467.
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Photochem Photobiol Sci. 2015 Apr;14(4):726-36. doi: 10.1039/c4pp00452c.

Photochemistry of N-(selenoalkyl)-phthalimides. Formation of N, Se-heterocyclic systems.

Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology

Gabriela Oksdath-Mansilla, Adrián A Heredia, Juan E Argüello, Alicia B Peñéñory

Affiliations

  1. INFIQC-CONICET, Dpto. de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA Córdoba, Argentina. [email protected] [email protected].

PMID: 25597467 DOI: 10.1039/c4pp00452c

Abstract

A variety of N-(selenomethyl)alkyl-phthalimides (alkyl = -(CH2)n-; n = 2-5, 1a, b, d, e) and N-(selenobenzyl)propyl phthalimide (1c) were synthesized and their photochemistry was studied at λ = 300 nm. Steady-state photolysis and laser time-resolved spectroscopy studies confirmed that these reactions proceeded by direct or acetone-sensitized excitation followed by intramolecular electron transfer (ET) between Se atom and the phthalimide moiety. Two main pathways are possible after ET: proton transfer to the ketyl radical anion from the CH3Se(+)˙ or the -CH2Se(+)˙- moieties, yielding the corresponding biradicals. Collapse of these biradicals yields cyclization products with the respective endo or exo selenium-containing heterocycles. Competition between both proton transfer processes depends on the chain length of the alkyl spacer between the phthalimide and Se groups as well as the size of the cycle being formed.

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