Cubane is the new Benzene

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Cubanes are a pretty neat class of molecules – in this video, we explore the applications of cubanes, and rank some impressive cubanes such as BUTTERCUBE!

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*Team*
Writer/Producer - That Chemist (Joey)
Editor/Lead Animator - ReformLabs
3D Systems Engineer - Robot Chicken
Thumbnail Artist - RinFroggy
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*Acknowledgements*
Thanks to the people on Twitter who helped suggest cubane references! Especially Kitspiroplatin for the reference of the extremely long tetracubane iodide! I also want to acknowledge that Tom will eventually make cubane.
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*References*
Tom’s Cubane Series https://www.youtube.com/playlist?list=PLnafk93vhO36cccP0p83hcop3xBTYkoTN
Perfluorocubane https://www.youtube.com/watch?v=Tn9EANWD96s
Chemiolis Click Chem https://www.youtube.com/watch?v=Ekbqix9fKXQ
Casual Chemistry Click Chem https://www.youtube.com/watch?v=RqA4xQ4ujWI

Cubane Review Articles:
Cubanes in Med Chem http://doi.org/10.1021/acs.jmedchem.8b00888
Cubanes: 50 Years Later http://doi.org/10.1021/cr500523x

Bicubyl/extremely long cubane https://pubs.acs.org/doi/10.1021/ja983441f
bidentate cubane ligand https://doi.org/10.1055/s-0029-1217083
butter cubane https://doi.org/10.1016/S0040-4039(00)73295-3
carboxycubane thioxanthylglycine - https://worldwide.espacenet.com/patent/search?q=pn%3DWO2004024709 (page 48)
cubane carboxylic acid https://doi.org/10.1002/chem.201901086
cubane dicarboxylic acid dimethyl ester https://doi.org/10.1055/s-0040-1705964
cubane https://doi.org/10.1055/s-1995-3961
cubene https://doi.org/10.1021/ja00229a057
cubyl phenyl ketone https://pubs.rsc.org/en/content/articlelanding/2019/OB/C9OB01238A
cubyl triflate https://pubs.acs.org/doi/abs/10.1021/ja00164a063
cubylmethanol https://doi.org/10.1021/ol501750k
dideuterocubane https://pubs.acs.org/doi/10.1021/jp953432i
diethynyl cubane https://pubs.acs.org/doi/abs/10.1021/ja00096a016
diflucuburon https://doi.org/10.1002/anie.201510675
letepricube https://worldwide.espacenet.com/patent/search?q=pn%3DWO2011068881
mercury cubane insanity https://doi.org/10.1021/cr500523x (compound 71)
methoxycarbonylcubane carboxylic acid - 10.1002/chem.201901086
octamethylcubane https://doi.org/10.1016/S0040-4039(00)73295-3
octacyclopropylcubane https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.200605150
octanitrocubane https://doi.org/10.1002/(SICI)1521-3773(20000117)39:2%3C401::AID-ANIE401%3E3.0.CO;2-P (this DOI sucks)
octaphenylcubane https://pubs.acs.org/doi/abs/10.1021/jo01058a537
perfluorocubane https://doi.org/10.1126/science.abq0516
perfluorooctamethylcubane https://pubs.acs.org/doi/abs/10.1021/ja00430a050
tetracarbomethoxycubane https://link.springer.com/article/10.1007/BF01665973
lead/tin cubane insanity/tetrabromotetranitrocubane https://pubs.acs.org/doi/10.1021/jo971308k
cubane on a pedestal - https://doi.org/10.1002/anie.199214211
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*Molecules in this Tierlist*
Bicubyl, bidentate cubane ligand, butter cubane, carboxycubane thioxanthylglycine, cubane carboxylic acid, cubane dicarboxylic acid dimethyl ester, cubane, cubene, cubyl phenyl ketone, cubyl triflate, cubylmethanol, dideuterocubane, diethynyl cubane, diflucuburon, letepricube, mercury cubane insanity, methoxycarbonylcubane carboxylic acid, octamethylcubane, octacyclopropylcubane, octanitrocubane, octaphenylcubane, perfluorocubane, perfluorooctamethylcubane, tetrabromotetranitrocubane, tetracarbomethoxycubane, tin cubane insanity, extremely long cubane, lead cubane insanity, cubane on a pedestal.
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