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Quadricyclane

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Quadricyclane is a strained, multi-cyclic hydrocarbon with the formula CH2(CH)6. A volatile colorless liquid, it is highly strained molecule (78.7 kcal/mol). Isomerization of quadricyclane proceeds slowly at low temperatures. Because of quadricyclane's strained structure and thermal stability, it has been studied extensively.

Preparation

Quadricyclane is produced by the irradiation of norbornadiene (bicyclo[2.2.1]hepta-2,5-diene) in the presence of Michler's ketone or ethyl Michler's ketone. Other sensitizers, such as acetone, benzophenone, acetophenone, etc., may be used but with a lesser yield. The yield is higher for freshly distilled norbornadiene, but commercial reagents will suffice. :[[File:Synthesis of quadricyclane from norbornadiene.png|400px]]

Proposed applications to solar energy

The conversion of norbornadiene into quadricyclane is achieved with ~300 nm UV radiation.{{cite book|url = https://books.google.com/books?id=Zr7algbSigoC&pg=PA366|page = 366|title = Organic Reactions And Their Mechanisms

Reactions

Quadricyclane readily reacts with acetic acid to give a mixture of nortricyclyl acetate and exo-norbornyl acetate.

Notes

References

  1. Petrov, V. A; Vasil’ev, N. V. “Synthetic Chemistry of Quadricyclane.” ''Current Organic Synthesis'' 3 (2006): 215–259
  2. Cahill, P; Steppel, R. Process of quadricyclane production. {{US patent. 10661194 filed September 12, 2003, and issued March 18, 2004
  3. Dubonosov, A. D; Bren, V. A; Chernoivanov, V. A. “Norbornadiene – quadricyclane as an abiotic system for the storage of solar energy.” ''Russian Chemical Reviews'' 71 (2002): 917–927
  4. (1983). "Norbornadiene-quadricyclane system in the photochemical conversion and storage of solar energy". Industrial & Engineering Chemistry Product Research and Development.
  5. (2003). "Thermal decomposition of high-energy density materials at high pressure and temperature". Journal of Analytical and Applied Pyrolysis.
  6. Smith, Claiborune D.. (1971). "Quadricyclane".
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hydrocarbons cyclopropanes tetracyclic-compounds
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