98%
921
2 minutes
20
In this study, we report the activation of molecular oxygen by 2,3-dihydropyrrole in endoperoxide mode. The endoperoxide is converted to a 1,4-dioxane derivative upon decomposition. This reaction proceeded stepwise without the use of any catalyst. Additionally, we isolated several intermediates that were characterized by single-crystal X-ray diffraction. Notably, one of the intermediates represents the first example of a structurally characterized 8-membered cyclic organic peroxide containing two endoperoxide groups and the direct conversion of an enamine to a dioxane has not been documented in the existing literature.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.joc.5c01396 | DOI Listing |
J Org Chem
September 2025
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
In this study, we report the activation of molecular oxygen by 2,3-dihydropyrrole in endoperoxide mode. The endoperoxide is converted to a 1,4-dioxane derivative upon decomposition. This reaction proceeded stepwise without the use of any catalyst.
View Article and Find Full Text PDFChemistry
August 2024
Department of chemistry, Indian Institute of Technology Guwahati, Guwahati, 781039, India.
Demonstrated here is an external photo-sensitizer-free (auto-sensitized) singlet oxygen-enabled solvent-dependent tertiary hydroxylation and aryl-alkyl spiro-etherification of C3-maleimidated quinoxalines. Such "reagent-less" photo-oxygenation at Csp-H and etherification involving Csp-H/Csp-H are unparalleled. Possibly, the highly π-conjugated N-H tautomer allows the substrate to get excited by irradiation, and subsequently, it attains the triplet state via ISC.
View Article and Find Full Text PDFJ Am Chem Soc
January 2020
Madrid Institute for Advanced Studies in Nanoscience (IMDEA Nanociencia), C/Faraday 9 , Madrid 28049 , Spain.
A combination of time-resolved optical spectroscopy and nanoscale imaging has been used to study the complex binding to amyloids of a photocatalyst that selectively photo-oxygenates pathogenic aggregates, as well as the consequences of its irradiation. Correlative atomic force microscopy (AFM) and fluorescence microscopy reveals topography-dependent binding of the dye to model β-lactoglobulin fibers, which may also explain the observed difference in their response to photodegradation. We provide direct evidence of the photosensitization of singlet oxygen by the photocatalyst bound to amyloid fibers by direct detection of its NIR phosphorescence.
View Article and Find Full Text PDF