The evolution of molecular belts and collars

Franz H. Kohnke, J. Fraser Stoddart

Research output: Contribution to journalArticlepeer-review

45 Scopus citations

Abstract

The Diels-Alder reaction has been employed to synthesise a hexaepoxyoctacosahydro[12]cyclacene derivative 6 in a highly efficient manner from the syn-isomer 1 of 1,4:5,8-diepoxy-1,4,5,8-tetrahydroanthracene and 2,3,5,6-tetramethylene-7-oxabicyclo[2.2.1]heptane 2. Each time a new cyclohexene ring is formed in the macropolycyclisation process, which utilises two molar equivalents of both the bisdienophile 1 and the bisdiene 2, the cycloadditions are trebly diastereoselective. A sequence of reactions on compound 6 involving (i) deoxygenation, (ii) dehydration, and (iii) partial hydrogenation have led to the isolation and characterisation of the D6h symmetrical dodecahydro[12]cyclacene derivative 10 containing six benzene rings. The synthetic strategy is new and the macropolycyclic compounds, which can be prepared according to this kind of molecular’LEGO’, are novel.

Original languageEnglish (US)
Pages (from-to)1581-1586
Number of pages6
JournalPure and Applied Chemistry
Volume61
Issue number9
DOIs
StatePublished - Jan 1 1989

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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