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Tetracyclo[2.2.0.02,6.03,5]hexane

Tetracyclo[2.2.0.02,6.03,5]hexane Struktur
650-42-0
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

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]
synthesis of prismane

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

Tetracyclo[2.2.0.02,6.03,5]hexane Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


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  • Tetracyclo[2.2.0.02,6.03,5]hexane
  • Prismane
  • 650-42-0
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