Cubanes, Fenestranes, Ladderanes, Prismanes, Staffanes and Other Oligocyclobutanoids

Abstract

Introduction Preparation of Oligocyclobutanoid Systems From Rigid to Flexible Oligo‐ and Polymeric Cyclobutanes

Pilot-Scale Production of Dimethyl 1,4-Cubanedicarboxylate

“…The allure of molecules with structures that differ significantly from those typically produced by terrestrial organisms has provided tremendous impetus for chemists to attempt their synthesis, explore their physical properties and chemical reactivity, and investigate their practical applications. − The C 8 H 8 hydrocarbon molecule, cubane ( 1 ) (Figure ), the second member of the five convex, uniform polyhedral, also known as the Platonic solids, is an example of such unusual molecules; it features eight carbon atoms in an essentially perfect cubic arrangement, and eight hydrogen atoms, one at each of the eight vertices, completing the valency requirements of carbon. The result is a compact, spherical molecular entity that belongs to the octahedral point group O h and possesses cubic symmetry .…”

The Joining of Measurement and Prediction: The Enthalpy of Formation of 1,4-Cubanedicarboxylic Acid

“…Cubane (pentacyclo[4.2.0.0 2,5 .0 3,8 .0 4,7 ]octane) and its derivatives are saturated polycycloalkanes in which there has been considerable interest , because of their high strain energy, multiple substitution possibilities, symmetry, and structural aesthetics alike. Soon after the first successful synthesis of the parent hydrocarbon in 1964, the enthalpies of formation of the parent hydrocarbon in the solid and gas phases were determined using combustion calorimetry and mass effusion .…”

A solid-state trimerisation of a diene diacid affords a bicyclobutyl: reactant structure from X-ray powder data and product separation and structure determination viaco-crystallisation

“…7 Chemists have typically employed solution-based methods to synthesize bicyclobutyls. 8 Transformations based on metalmediated couplings using Grignard and lithium reagents, as well as free radical and anionic-initiated polymerizations of functionalized cyclobutanes, have been reported.…”