OKSDATH-MANSILLA GABRIELA
Artículos
Título:
Photochemistry of N-(selenoalkyl)-Phthalimides. Formation of N, Se-heterocyclic
Autor/es:
OKSDATH MANSILLA, GABRIELA; PEÑÉÑORY, ALICIA B.; HEREDIA, ADRIÁN A.; ARGÜELLO, JUAN E.; PEÑEÑEORY, ALICIA A
Editorial:
ROYAL SOC CHEMISTRY
Referencias:
Lugar: CAMBRIDGE; Año: 2015
Resumen:
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 studied at λ = 300 nm.
Steady-state photolysis and laser time-resolved spectroscopic studies confirmed that these reactions
proceeded by direct or acetone-sensitized excitation followed by intramolecular electron transfer (ET)
between the phthalimide moiety and Se atom. 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 respectively endo or exo
selenium-containing heterocycles. Competition between both proton transfers 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.