ortho-Tolyl(trifluoromethyl)carbenes:Generation, Calculations, and Reactions through Quantum Mechanical Tunneling

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Authors

Zhu, Chengliang

Issue Date

2012

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Thesis

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1 , 4-H migration , Carbene , DFT calculation , o-Tolyl(trifluoromethyl)carbene , Reactive intermediate , Tunneling

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We synthesized o-tolyl(trifluoromethyl)diazirine, trideuteriomethyl-o-tolyl(trifluoromethyl)diazirine and p-methoxy-o-tolyl(trifluoromethyl)diazirine precursors and generated the corresponding carbene species photochemically in low temperature nitrogen matrices. 1, 4-Hydrogen shifts in thermal decay and other photochemical reactivities were investigated both experimentally and theoretically. All carbene species as well as their subsequent rearranged products were characterized with IR and UV-vis spectroscopy and confirmed by comparison with frequency and TD DFT calculations at the B3LYP/6-31G** level of theory.

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