Tetracyclo[2.2.0.02,6.03,5]hexane
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- CAS-Nr.
- 650-42-0
- Englisch Name:
- Tetracyclo[2.2.0.02,6.03,5]hexane
- Synonyma:
- Prismane;Tetracyclo[2.2.0.02,6.03,5]hexane
- CBNumber:
- CB52414426
- Summenformel:
- C6H6
- Molgewicht:
- 78.11
- MOL-Datei:
- 650-42-0.mol
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Tetracyclo[2.2.0.02,6.03,5]hexane Eigenschaften
- Siedepunkt:
- 75.86°C (rough estimate)
- Dichte
- 0.8155 (estimate)
- Brechungsindex
- 1.4770 (estimate)
Sicherheit
Tetracyclo[2.2.0.02,6.03,5]hexane Chemische Eigenschaften,Einsatz,Produktion Methoden
Synthese
Katz and Acton's original synthesis of prismane(Tetracyclo[2.2.0.02,6.03,5]hexane) starts from benzvalene (1) and 4-phenyltriazolidone (2), which is a strong dienophile. The reaction is a stepwise Diels-Alder like reaction, forming a carbocation as intermediate. The adduct (3) is then hydrolyzed under basic conditions and afterwards transformed into a copper(II) chloride derivative with acidic copper(II) chloride. Neutralized with a strong base, the azo compound (5) could be crystallized with 65% yield. The last step is a photolysis of the azo compound. This photolysis leads to a biradical which forms prismane (6) and nitrogen with a yield of less than 10% (in Katz and Acton's work, 1.8%, but subsequently improved).
[1]
Einzelnachweise
[1]Katz T. J.; Acton N. (1973). "Synthesis of Prismane".Journal of the American Chemical Society.95(8):2738–2739.Bibcode:1973JAChS..95.2738K.doi:10.1021/ja00789a084
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Edge Rate |
- Tetracyclo[2.2.0.02,6.03,5]hexane
- Prismane
- 650-42-0