5943-40-8Relevant articles and documents
Iodide-Catalyzed Selenium-Assisted Sequential Multicomponent Synthesis of a Luminescence Benzo-Oxazino-Isoindole Framework
Sedighian, Hadi,Mamaghani, Mohammad Barasm,Notash, Behrouz,Bazgir, Ayoob
, p. 2244 - 2253 (2021)
We have described an unexpected pathway using the R-NC/Se system for the synthesis of the unreported benzo-oxazino-isoindole framework by the iodide-catalyzed selenium-assisted sequential multicomponent reaction of the Knoevenagel adduct of ninhydrin and
Alkanethioimidoyl Radicals: Evaluation of β-Scission Rates and of Cyclization onto S-Alkenyl Substituents
Minozzi, Matteo,Nanni, Daniele,Walton, John C.
, p. 2056 - 2069 (2007/10/03)
Thioimidoyl radicals were generated by addition of alkylsulfanyl radicals to alkyl isonitriles and were characterized by electron paramagnetic resonance (EPR) spectroscopy. The β-scissions of their C·S-C bonds were studied by variable-temperature EPR spectroscopy and the fragmentation rate constants and activation energies were calculated. The scission rates depend on the stability of the released alkyl radicals but in any case, at room temperature, the processes were fast. Data collected on similar oxyimidoyls showed that their fragmentations are slightly slower compared to those of analogous thioimidoyls. The scission rates of selenoimidoyls could not be studied by EPR and were evaluated by theoretical calculations. EPR experiments also enabled both β-scission and 5-exo ring closure rate constants of two S-but-3-enyl-substituted imidoyl radicals to be determined, showing that cyclization prevails only at low temperatures. Density functional theory (DFT) theoretical calculations predicted that the fragmentation process preferentially occurs from the s-cis rotamers (X-C bond) of the imidoyl radicals. Thio- and seleno-imidoyls (but not oxyimidoyls) prefer s-trans conformations so that their fragmentations involve prior rotation about the X-C bond.
