All-Carbon Molecules: Evidence for the Generation of Cyclo[18]carbon from a Stable Organic Precursor

Science  08 Sep 1989:
Vol. 245, Issue 4922, pp. 1088-1090
DOI: 10.1126/science.245.4922.1088


The unambiguous structural characterization of a single-sized all-carbon molecule requires its chemical synthesis. For cyclo[18]carbon, ab initio calculations predict a relatively stable, cyclic D9h ground state geometry with alternating C-C (1.36 angstroms) and C≡C (1.20 angstroms) bonds. The synthesis and x-ray crystal structure of a direct precursor to C18 are described. The analysis of laser flash heating experiments on this precursor by time-of-flight mass spectroscopy shows a sequence of retro-Diels-Alder reactions leading to C18 as the predominant fragmentation pattern. Structural evidence is provided for the generation of an all-carbon molecule from a well-characterized organic precursor.

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