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Pentagonal dodecahedranes: polyfunctionalization and MS fragmentation.

P Landenberger1, K Scheumann, M Keller

  • 1Chemisches Laboratorium der Universität Freiburg i. Br., Institut für Organische Chemie und Biochemie, Albertstrasse 21, D-79104 Freiburg i.Br., Germany.

The Journal of Organic Chemistry
|August 21, 2001
PubMed
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Researchers explored creating strained dodecahedranes with vicinal bromine substituents. They found challenges in radical and cationic intermediate interception, with varying success for different halogens and functional groups.

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Dodecahedranes are highly symmetrical C20H20 molecules with unique cage structures.
  • Functionalization of dodecahedranes presents synthetic challenges due to steric hindrance and cage strain.
  • Exploring strained polycyclic hydrocarbons is crucial for understanding fundamental chemical bonding and developing novel materials.

Purpose of the Study:

  • To investigate the synthesis of highly strained dodecahedranes featuring vicinal, eclipsed bromine substituents.
  • To explore the reactivity of dodecahedranes with various functional groups under radical and cationic conditions.
  • To characterize the structural and electronic consequences of introducing significant molecular strain.

Main Methods:

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  • Utilized four- to eight-fold functionalized dodecahedranes as starting materials.
  • Employed front-side substitution and addition reactions to introduce bromine substituents.
  • Characterized reaction intermediates and products using X-ray crystallography and mass spectrometry (MS).

    • Main Results:

    • Successfully synthesized strained dodecahedranes with two to four pairs of vicinal, eclipsed bromine substituents.
    • Observed differential reactivity in the interception of radical and cationic intermediates depending on the halogen (Cl vs. Br) and functional group.
    • X-ray analyses revealed significant structural consequences of molecular strain due to vicinal substituent pairs.
    • Mass spectrometry confirmed substituent elimination without carbon-cage disruption, yielding unsaturated dodecahedral ions.

    Conclusions:

    • The study demonstrates feasible routes to highly strained, functionalized dodecahedranes.
    • The regioselectivity and efficiency of radical/cationic intermediate interception are highly dependent on the specific reaction conditions and substituents.
    • The inherent stability of the dodecahedrane cage allows for significant functionalization and strain introduction without skeletal fragmentation.