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Molecular dynamics-guided reaction discovery reveals endoperoxide-to-alkoxy radical isomerization as key branching point in α-pinene ozonolysis.
Nat Commun
January 2025
Department of Chemistry, University of Helsinki, Helsinki, Finland.
Secondary organic aerosols (SOAs) significantly impact Earth's climate and human health. Although the oxidation of volatile organic compounds (VOCs) has been recognized as the major contributor to the atmospheric SOA budget, the mechanisms by which this process produces SOA-forming highly oxygenated organic molecules (HOMs) remain unclear. A major challenge is navigating the complex chemical landscape of these transformations, which traditional hypothesis-driven methods fail to thoroughly investigate.
View Article and Find Full Text PDFTracking the Geometric and Positional Isomerization of Lipid C═C Bonds in the Bacterial Stress Responses by Mass Spectrometry.
Anal Chem
January 2025
The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei 430072, China.
The position and configuration of the C═C bond have a significant impact on the spatial conformation of unsaturated lipids, which subsequently affects their biological functions. Double bond isomerization of lipids is an important mechanism of bacterial stress response, but its in-depth mechanistic study still lacks effective analytical tools. Here, we developed a visible-light-activated dual-pathway reaction system that enables simultaneous [2 + 2] cycloaddition and catalytic - isomerization of the C═C bond of unsaturated lipids via directly excited anthraquinone radicals.
View Article and Find Full Text PDFFrom Beam Damage to Massive Reaction Amplification under the Electron Microscope: An Ionization-Induced Chain Reaction in Crystals of a Dewar Benzene.
ACS Cent Sci
December 2024
Department of Chemistry and Biochemistry, University of California at Los Angeles, Los Angeles, California 90095, United States.
Article Synopsis
- Electron microscopy is a powerful technique in nanotechnology, but it often causes random damage to samples being studied.
- The introduction of a specific chemical probe can effectively manage this damage, allowing for clearer characterization of the interactions between electron beams and soft organic materials.
- In experiments with Dewar benzene crystals subjected to a high-energy electron beam, researchers observed a significant increase in chemical reactions, amplifying the events by up to 90,000 times per incident electron.
Assembly of Pyrenes through a Quadruple Photochemical Cascade: Blocking Groups Allow Diversion from the Double Mallory Path to Photocyclization at the Bay Region.
J Am Chem Soc
January 2025
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.
We present a six-step cascade that converts 1,3-distyrylbenzenes (-stilbenes) into nonsymmetric pyrenes in 40-60% yields. This sequence merges photochemical steps, ,-alkene isomerization, a 6π photochemical electrocyclization (Mallory photocyclization); the new bay region cyclization, with two radical iodine-mediated aromatization steps; and an optional aryl migration. This work illustrates how the inherent challenges of engineering excited state reactivity can be addressed by logical design.
View Article and Find Full Text PDFCatalytic Aerobic Carbooximation of Alkenes Using Secondary Nitroalkanes as Both α-Nitro Alkyl Radical and Nitrogen Monoxide Sources.
Org Lett
January 2025
Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.
Aerobic nitro-nitrite isomerization of secondary nitroalkanes is postulated to proceed via the intermediacy of the α-nitro alkyl radical, where the corresponding Nef-type products, ketones, and nitrogen monoxide can be obtained as byproducts. To explore the catalytic aerobic carbooximation of alkenes using secondary nitroalkanes, phase-transfer catalysis of KSeCN and TBAI has been developed. The current aerobic carbooximation of alkenes utilizes nitroalkanes as both radical and nitrogen monoxide sources in water without external oxidants and prefunctionalized nitroalkanes.
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