Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 15, Issue -, Pages 1552-1562Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.15.158
Keywords
alkanes; carbocations; DFT; oxidations; ruthenium tetroxide
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Funding
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2016-76155-R]
- Fondos Europeos para el Desarrollo Regional (FEDER)
- Gobierno de Aragon (Zaragoza, Spain) [E34-R17]
- University of Catania
- University of Pavia
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The ruthenium tetroxide-mediated oxidation of cyclopentane, tetrahydrofuran, tetrahydrothiophene and N-substituted pyrrolidines has been studied computationally by DFT and topological (analysis of the electron localization function, ELF) methods. In agreement with experimental observations and previous DFT calculations, the rate-limiting step of the reaction takes place through a highly asynchronous (3 + 2) concerted cycloaddition through a single transition structure (one kinetic step). The ELF analysis identifies the reaction as a typical one-step-two-stages process and corroborates the existence of a transient carbocation. In the case of pyrrolidines, the carbocation is completely stabilized as an energy minimum in the form of an iminium ion and the reaction takes place in two steps.
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