The highly symmetrical C8H8 hydrocarbon cubane was first synthesized by Philip Eaton in 1964. Before that, many thought that it could not be synthesized because of the great strain generated by its 90° C–C–C bond angles. Cubane is isomeric with cyclooctatetraene, and this relationship has been used to synthesize cyclooctatetraenophanes from cubane-derivative building blocks.
January 2, 2023
As its name implies, Cubane1 is a highly symmetrical cubic molecule. It is thermally unstable because of the high strain of its 90° bond angles.
In December, Xujun Cheng, Stephen L. Craig, and co-workers at Duke University (Durham, NC) described the mechanochemistry of cubane. When a cubane derivative with polymeric side chains at the 1- and 2-positions was subjected to pulsed ultrasonication, the only product was the corresponding syn-tricyclooctadiene, in contrast to the cyclooctatetraene derivative formed by thermal isomerization.
1. CAS Reg. No. 277-10-1.
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