Add time:09/09/2019 Source:sciencedirect.com
Gas phase thermolyses of 3,6-dimethyl, -diethyl and -di-n-propyl substituted 1,2,3,6-tetrahydro-1,2,4,5-tetrazines 1a–1c yielded the corresponding N-unsubstituted imines 2a–2c. The He(I) photoelectron spectra of propanimine (2b) and butanimine (2c) are presented for the first time. First ionization potentials and orbital energies of the imines as determined with B3LYP/6-31+G*//HF/6-31+G* reproduce the experimental data. Ionization bands arising from N,N′-unsubstituted diazetidines 3a–3c could not be detected in the pyrolysis spectra of 1a–1c. Calculations for the extrusion of nitrogen from tetrahydrotetrazine 1a resulted in a transition state for a [2+2+2]-cycloreversion that leads to the imine 2a as product.
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