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Tetracyclo[2.2.0.02,6.03,5]hexane

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Tetracyclo[2.2.0.02,6.03,5]hexane Basic information
Product Name:Tetracyclo[2.2.0.02,6.03,5]hexane
Synonyms:Tetracyclo[2.2.0.02,6.03,5]hexane;Prismane
CAS:650-42-0
MF:C6H6
MW:78.11
EINECS:
Product Categories:
Mol File:650-42-0.mol
Tetracyclo[2.2.0.02,6.03,5]hexane Structure
Tetracyclo[2.2.0.02,6.03,5]hexane Chemical Properties
Boiling point 75.86°C (rough estimate)
density 0.8155 (estimate)
refractive index 1.4770 (estimate)
Safety Information
MSDS Information
Tetracyclo[2.2.0.02,6.03,5]hexane Usage And Synthesis
Synthesis 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
References [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 Preparation Products And Raw materials
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