3 years ago

Propellanes—From a Chemical Curiosity to “Explosive” Materials and Natural Products

Propellanes—From a Chemical Curiosity to “Explosive” Materials and Natural Products
Stefan Bräse, Eduard Spuling, Alicia M. Dilmaç, Armin de Meijere
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. Exploding class: Propellanes are a unique class of compounds with well over 10 000 members having inverted tetrahedral carbon atoms at their bridgehead positions that are linked through a weak single bond. These propeller-type compounds are not only structurally interesting, they also exhibit unusual reactivities. This Review highlights their syntheses and applications in material sciences, natural product synthesis, and medicinal chemisty.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201603951

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