Editing Cubane (section)

===Persubstituted derivatives===
Octaphenylcubane pre-dates the parent compound.  Freedman synthesized it from [[tetraphenylcyclobutadiene nickel bromide]] in 1962. It is a sparingly soluble colourless compound that melts at 425–427&nbsp;°C.<ref name= Biegasiewicz /><ref name=freedman1961 /><ref name=freedman1962 /><ref name=freedman1965 />  

[[Octanitrocubane]] is a [[green explosive]].  

Both [[heptafluorocubane]] and [[octafluorocubane]] were synthesized in 2022 to study octafluorocubane's unusual [[electronic structure]].<ref>{{cite journal |vauthors=Sugiyama M, Akiyama M, Yonezawa Y, Komaguchi K, Higashi M, Nozaki K, Okazoe T |date=August 2022 |title=Electron in a cube: Synthesis and characterization of perfluorocubane as an electron acceptor |journal=Science |volume=377 |issue=6607 |pages=756–759 |doi=10.1126/science.abq0516 |pmid=35951682 |bibcode=2022Sci...377..756S |s2cid=251515925}}</ref>  Single-electron reduction to the [[radical anion]] {{chem|C|8|F|8|-}} traps<ref>Pichierri, F. Substituent effects in cubane and hypercubane: a DFT and QTAIM study. ''Theor Chem Acc'' 2017; 136: 114. {{doi|10.1007/s00214-017-2144-5}}</ref> an otherwise-free electron inside the cube, making it the world's smallest box.<ref>{{cite journal |vauthors=Krafft MP, Riess JG |date=August 2022 |title=Perfluorocubane-a tiny electron guzzler |journal=Science |volume=377 |issue=6607 |pages=709 |doi=10.1126/science.adc9195 |pmid=35951708 |bibcode=2022Sci...377..709K |s2cid=251517529|url=https://hal.science/hal-03873082 }}</ref>