Hashikawa Yoshifumi, Sadai Shumpei, Murata Yasujiro
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Org Lett. 2021 Dec 17;23(24):9495-9499. doi: 10.1021/acs.orglett.1c03694. Epub 2021 Nov 22.
The decarbonylation of a cage-opened C derivative was examined by employing single-electron reductants. During the reaction, an HO molecule was spontaneously encapsulated inside the cage (up to 78%) through the thus-formed 14-membered-ring orifice even though the HO encapsulation had long been considered to require an orifice consisting of at least 16 atoms. The crystallographic analysis revealed an orifice shape closer to a circle which significantly contributes to the decreased activation barrier for the HO encapsulation.