Chemistry of Cage‐shaped Hydrocarbons. The Oxidation of Heptacyclo[6.6.0.0 2,6 .0 3,13 .0 4,11 .0 5,9 .0 10,14 ]tetradecane

Tahsin J. Chow*, Chin‐Chuan ‐C Wei, Tung-Kung Wu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

Oxidative ring opening reactions enabled disassembly of the cage structure of the title compound. Stepwise oxidations were achieved through radical intermediates using lead tetracetate and iodine. The regioselectivity of bond fission is rationalized by comparing the relative strains of each bond. Multiple cleavages of C‐C bond were accomplished by photolysis with HgO and iodine under UV. The oxidative effect of Ce(IV) ion on a cage‐shaped diketone is examined. New skeletons of polyquinanes are obtained from these reactions.

Original languageEnglish
Pages (from-to)833-841
Number of pages9
JournalJournal of the Chinese Chemical Society
Volume41
Issue number6
DOIs
StatePublished - 1 Jan 1994

Keywords

  • Cage compounds
  • Ceric oxidation
  • Heptacyclotetradecane
  • Hypoiodite oxidation
  • Polyquinanes

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