Chemistry

Explosive When Scratched

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Science  13 Dec 2002:
Vol. 298, Issue 5601, pp. 2095
DOI: 10.1126/science.298.5601.2095c

Cubane—a molecule consisting of eight carbon atoms at the corners of a cube with a hydrogen atom attached to each carbon—was first reported in 1964. Manini et al. have prepared an expanded cubane, in which C≡C-C≡C units connect each pair of adjacent corners. In their synthesis, two corners are joined to form an edge, two edges are linked to yield a face, and two faces are combined to produce a cube. The resulting structure contains 56 carbon atoms, and each corner is protected with a methoxy (-OCH3) group. Although this expanded cubane is highly strained and explosive, the authors were able to characterize the molecule with nuclear magnetic resonance and to verify its cubic symmetry. Mass spectrometry indicates that, upon loss of the methoxy groups, the molecule is not stable in the cubane geometry and converts to a fullerene. — JFU

Angew. Chem. Int. Ed.41, 4339 (2002).

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