Publications by authors named "Thomas Osswald"
As part of a study to achieve selective oligo(poly)bromination-ultimately perbromination-of the dodecahedral C(20) skeleton, the extent and direction of the ionic bromination of dodecahedrene and 1,16-dodecahedradiene were explored. Along sequences of Br(+) additions/deprotonations and allylic rearrangements, up to ten hydrogen atoms were substituted (traces of C(20)H(x)Br(10)). Tetrabromododecahedrenes obtained under defined conditions in up to 50 % total yield with three and four allylic bromine substituents protecting the extremely bent C==C bonds, proved highly unreactive even towards oxygen but reacted rapidly with CH(2)N(2).
View Article and Find Full Text PDFArticle 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.