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Unsaturated Dodecahedranes—In Quest of the C 20 H 14 1,4,16‐Triene and C 20 H 12 1,4,10(14),16‐Tetraene, and Their Cations and Anions
Author(s) -
Reinbold Jens,
Sackers Emmerich,
Oßwald Thomas,
Weber Klaus,
Weiler Andreas,
Voss Torsten,
Hunkler Dieter,
Wörth Jürgen,
Knothe Lothar,
Sommer Frank,
Morgner Nina,
von Issendorff Bernd,
Prinzbach Horst
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020118)8:2<509::aid-chem509>3.0.co;2-d
Subject(s) - ion , chemistry , cycloaddition , ionization , x ray photoelectron spectroscopy , ionization energy , cage , hydrogen , computational chemistry , photochemistry , crystallography , organic chemistry , catalysis , physics , mathematics , nuclear magnetic resonance , combinatorics
The highly pyramidal, highly strained C 20 H 14 1,4,16‐dodecahedratriene ( 4 ) and C 20 H 12 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 C 20 H 14 /C 2o H 12 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.