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Science 8 September 1989:
Vol. 245. no. 4922, pp. 1088 - 1090
DOI: 10.1126/science.245.4922.1088
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Articles

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

FRANÇOIS DIEDERICH 1, YVES RUBIN 1, CAROLYN B. KNOBLER 1, ROBERT L. WHETTEN 1, KENNETH E. SCHRIVER 1, KENDALL N. HOUK 1, and YI LI 1

1 Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90024.

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 CequivC (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.

Submitted on May 18, 1989
Accepted on July 10, 1989


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
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Cyclocarbon Coalescence: Mechanisms for Tailor-Made Fullerene Formation.
S. W. McElvany, M. M. Ross, N. S. Goroff, and F. Diederich (1993)
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The Higher Fullerenes: Isolation and Characterization of C76, C84, C90, C94, and C70O, an Oxide of D5h-C70.
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