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• W2560574560 abstract "Abstract In solution, pericyclic reactions have been shown to be greatly accelerated with near barrier-less energy surfaces and high efficiency as well as high stereo and regioselectivity by the use of reagents in their radical cation forms, that is, via “hole-catalyzed” cycloadditions. In this study, the intrinsic gas-phase [3 +  + 2] cycloaddition reactivity of two model nitrile N-oxides in their ionized forms, that is PhC N + O ( 1 ) and CH 3 C N + O ( 2 ) towards prototype dipolarophiles, that is several ketones, nitriles, and alkenes was investigated via pentaquadrupole MS 3 mass spectrometry. The competition between hole-catalyzed [3 +  + 2] cycloaddition and electron and/or proton transfer was evaluated and compared to proton affinities and ionization energies. With alkenes and ethers, 1 was found to react exclusively via proton and/or electron transfer. But with nitriles and ketones, cycloaddition occurred predominantly to yield abundant cycloadducts. MS 3 scans were used to probe the structures of the final products, whereas theoretical calculations served to evaluate the likehood of competing reactions. In great contrast to 1 and probably due to its greater acidity, 2 was found to react exclusively towards all dipolarophiles tested herein by either proton and/or electron transfer, or both." @default.
• W2560574560 created "2016-12-16" @default.
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• W2560574560 date "2017-07-01" @default.
• W2560574560 modified "2023-10-02" @default.
• W2560574560 title "“Hole-catalyzed” cycloadditions of the gaseous ionized nitrile N-oxides Ph-C N+O and CH3C N+O with model dipolarophiles" @default.
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• W2560574560 doi "https://doi.org/10.1016/j.ijms.2016.12.009" @default.
• W2560574560 hasPublicationYear "2017" @default.
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