AI Article Synopsis
- The compounds 1,4,16-dodecahedratriene (4) and 1,4,10(14),16-dodecahedratetraene (5) are unique cage olefins with interesting properties related to their internal structure.
- DFT calculations provide insights into the effects of one- and two-electron oxidation and reduction on the energetics and geometry of compound 5.
- Efforts to synthesize these compounds using specific thermal reactions were unsuccessful, but their anions and cations can be generated through electron impact or ionization, though challenges in mass-selection were encountered due to low ion intensity and structural instability.
Article Abstract
The highly pyramidal, highly strained 1,4,16-dodecahedratriene (4) and C20H12 1,4,10(14),16-dodecahedratetraene (5) are cage olefins with an intriguing "inner life". For 5 DFT calculations give information about the energetic and geometrical consequences of one-/two-electron oxidation and reduction. Attempts to prepare 4 and 5 through thermal retro[2+2]/[4+2]cycloaddition strategies proved unsuccessful. Still, the C20H14/C20H12 cage cations and anions are liberated upon electron impact or gas-discharge ionization of their thermally extremely stable tris-/tetrakisanthraceno-anellated derivatives. Mass-selection (photoelectron (PE) characterization) of the anions failed, however, due to the very small anion intensity, the preferential formation of hydrogen-poor ions, and minor cage disruption.
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| http://dx.doi.org/10.1002/1521-3765(20020118)8:2<509::AID-CHEM509>3.0.CO;2-D | DOI Listing |
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