title: Propellanes-From a Chemical Curiosity to "Explosive" Materials and Natural Products.
abstract: Propellanes are a unique class of compounds currently consisting of well over 10 000 representatives, all featuring two more or less inverted tetrahedral carbon atoms that are common to three bridging rings. The central single bond between the two bridgeheads is significantly weakened in the smaller entities, which leads to unusual reactivities of these structurally interesting propeller-like molecules. This Review highlights the synthesis of such propellanes and their occurrence in material sciences, natural products, and medicinal chemistry. The conversion of [1.1.1]propellane into bridgehead derivatives of bicyclo[1.1.1]pentane, including oligomers and polymers with bicyclo[1.1.1]penta-1,3-diyl repeat units, is also featured. A selection of natural products with larger propellane subunits are discussed in detail. Heteropropellanes and inorganic propellanes are also addressed. The historical background is touched in brief to show the pioneering work of David Ginsburg, Günther Snatzke, Kenneth B. Wiberg, Günter Szeimies, and others.
authors.affiliation: Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Alicia M
authors.initials: AM
authors.lastname: Dilmaç
authors.affiliation: Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Eduard
authors.identifier: 0000-0002-6881-9018
authors.initials: E
authors.lastname: Spuling
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August Universität Göttingen, Tammannstrasse 2, 37077, Göttingen, Germany.
authors.forename: Armin
authors.identifier: 0000-0002-5140-0720
authors.initials: A
authors.lastname: de Meijere
authors.affiliation: Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.|Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), Eggenstein-Leopoldshafen, Germany.
authors.forename: Stefan
authors.identifier: 0000-0003-4845-3191
authors.initials: S
authors.lastname: Bräse
keywords: functional materials; natural products; pharmacological activity; propellanes; staffanes