A beautiful molecule

OK class.  Pop quiz.  Draw the structure of C304 H264 (not a misprint).  To help you out there are 6 sharp NMR peaks (roughly the same size) between 7.8 and 8.5, a doublet at 8.6  and a large peak at 1.45.  This obviously tells you the molecule is quite symmetric.

Give up?   You can read about it’s elegant synthesis and structure in  Science vol. 363 pp. 151 – 155 ’19.  I doubt that Woodward ever thought of a molecule like this, but do not doubt that he would have loved the elegance of its synthesis, using techniques and reagents not available to him years ago.

Give up?  Does the fact the the molecule contains 40 benzene moieties help?  How about the 16 tButyl groups?

Does the fact that the dimensions of the molecule are 17.4 x 16.4 x 16.4 Angstroms help?  How about the fact that the molecule contains a central space which can comfortably fit a buckyball inside?

I’ll fill in some details tomorrow for those without access to the paper.  I’d love to see the NMR of a cyclophane derivative (which the authors haven’t made yet).

Bravo to all concerned in the paper.

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