New Aspects of Highly Strained Ring Chemistry

  • Z. Yoshida
Part of the NATO ASI Series book series (ASIC, volume 273)

Abstract

Electronic features of small ring systems are described. Control of stability and reactivity of highly strained systems has been achieved thru modification with substituents. Thus, the diaminochlorocyclopropenium ion, its Grignard reagent or lithium carbenoid are shown to be useful building blocks for the introduction of a diamino-cyclopropenylidene moiety. The trithiocyclopropenium ion is a versatile building block in the synthesis of heterocycles. A theoretically interesting 16π aromatic hydrocarbon, “cyclic bicalicene” was synthesized on the basis of the dithiodichlorocyclopropene strategy. A new type of molecular energy storage system involving a photovalence isomerization to a highly strained system is described for a donor-acceptor substituted norbornadiene going to the corresponding quadricyclane (“DONAC”), as well as a bulkily substituted polyacene going to the corresponding valene isomer (“AROVA”). The concept and experimental data for DONAC as an excellent solar energy storage system are shown in detail. Both systems, in particular the former will be candidates for an information storage system.

Keywords

Quantum Yield High Occupied Molecular Orbital Lower Unoccupied Molecular Orbital Secondary Amine High Occupied Molecular Orbital 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • Z. Yoshida
    • 1
  1. 1.Department of Synthetic ChemistryKyoto UniversityYoshida, KyotoJapan

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