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.
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© 1989 Kluwer Academic Publishers
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Yoshida, Z. (1989). New Aspects of Highly Strained Ring Chemistry. In: de Meijere, A., Blechert, S. (eds) Strain and Its Implications in Organic Chemistry. NATO ASI Series, vol 273. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0929-8_25
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DOI: https://doi.org/10.1007/978-94-009-0929-8_25
Publisher Name: Springer, Dordrecht
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