Transformation of Imine Cages to Hydrocarbon Cages

In contrast to organic cages which are formed by exploiting dynamic covalent chemistry, such as boronic ester cages, imine cages or disulfide cages, those with a fully carbonaceous backbone are rarer. With the exception of alkyne metathesis based approaches, the vast majority of hydrocarbon cages needs to be synthesized by kinetic bond formation. This implies a multiple step synthesis and no correction mechanism in the final macrocyclization step ‐ both responsible for low overall yields. Whereas for smaller cages the intrinsic drawbacks are not always obvious, larger cages are seldom synthesized in yields beyond a few tenth of a percent. Here we present a three‐step method to convert imine cages into hydrocarbon cages. This has been successfully applied even for larger structures such as derivatives of C72H72 – an unknown cage suggested by Fritz Vögtle more than 20 years ago.

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