Abstract:
Upon the photolysis (λ=546nm) of X-ray irradiated cyclopentene oxide/Freon solutions at 77K, irreversible proton abstraction in the ring-open form of the cyclopentene oxide radical cation occurs, affecting the bridgehead carbon. This affords unstable 6-oxabicyclo[3.1.0]hexan-1-yl radicals, which undergo rearrangement to form ring-open terminal C-centered alkyl radicals detected as final products.
Citation:
I. D. Sorokin, O. I. Gromov, V. I. Pergushov, D. A. Pomogailo, M. Ya. Melnikov, “Photoinduced deprotonation of cyclopentene oxide radical cations in low-temperature Freon matrices”, Mendeleev Commun., 30:1 (2020), 67–69
Linking options:
https://www.mathnet.ru/eng/mendc1103
https://www.mathnet.ru/eng/mendc/v30/i1/p67
This publication is cited in the following 7 articles:
Mikhail Ya. Melnikov, Oleg I. Gromov, Vladimir I. Pergushov, Daria A. Pomogailo, Ivan D. Sorokin, “PHOTOCHEMISTRY OF RADICAL CATIONS OF SOME ORGANIC OXYGEN-CONTAINING COMPOUNDS IN FROZEN MATRICES”, Lomonosov chemistry journal, 65:№3, 2024 (2024), 171
M. Ya. Melnikov, O. I. Gromov, V. I. Pergushov, D. A. Pomogailo, I. D. Sorokin, “Photochemistry of Radical Cations of Some Organic Oxygen-Containing Compounds in Frozen Matrices”, Moscow Univ. Chem. Bull., 79:3 (2024), 147
A. O. Naumova, P. V. Melnikov, V. A. Kuzmin, N. K. Zaitsev, “Features of photoinduced proton transfer in the presence of a polyelectrolyte”, Mendeleev Commun., 33:2 (2023), 212–214
Ivan D. Sorokin, Oleg I. Gromov, Vladimir I. Pergushov, Daria A. Pomogailo, Mikhail Ya. Melnikov, “Effect of Freon matrices on the intermediates stabilized in X-ray irradiated 1,7-dioxaspiro[5,5]undecane solutions at 77 K”, Mendeleev Communications, 31:3 (2021), 343
M. Ya. Melnikov, I. D. Sorokin, O. I. Gromov, V. I. Pergushov, D. A. Pomogailo, “Photochemistry of Oxirane-Derived Radical Cations in Freonic Matrices at 77 K”, Moscow Univ. Chem. Bull., 76:1 (2021), 1
A. O. Naumova, A. K. Afanasyev, P. V. Melnikov, N. K. Zaitsev, “Effect of micelles on pKa* of acridine: a spectroscopic study”, Mendeleev Commun., 31:6 (2021), 833–835
D. A. Pomogailo, I. D. Sorokin, O. I. Gromov, V. I. Pergushov, M. Ya. Melnikov, “Photochemical transformations of exo-2,3-norbornene oxide radical cations in the CF3CCl3 matrix at 77K”, Mendeleev Commun., 31:2 (2021), 154–156
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