The making of molecular belts and collars

J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

This article relates the first encouraging steps towards the fulfilment of a long-standing research goal aimed at turning the chemistry of laterally-fused six-membered rings through 90° ... or, more specifically, the making of (i) beltenes, in which 1,4-cyclohexadiene rings are linked in a polycyclic array by lateral fusion through their carbon-carbon double bonds, (ii) collarenes, in which alternating benzene and 1,4-cyclohexadiene rings are fused to form macropolycyclic hydrocarbons and (iii) cyclacenes, which may be considered as two annulenes joined to each other by carbon-carbon single bonds between every other atom around the annulene rings. The synthesis of the key macropolycyclic compound, which is a potential precursor of [12]beltene and [12]collarene, exploits the amazing stereoelectronic control that exists in the Diels-Alder reaction between a bisdiene and a bisdienophile with the appropriate structural features and reactivity characteristics.

Original languageEnglish (US)
Pages (from-to)227-245
Number of pages19
JournalJournal of Inclusion Phenomena and Molecular Recognition in Chemistry
Volume7
Issue number2
DOIs
StatePublished - Apr 1989

Keywords

  • Cavitands
  • Diels-Alder reactions
  • [12]beltene
  • [12]collarene
  • [12]cyclacene
  • chemical sensor
  • clathrate formation
  • kohnkene
  • organic zeolites
  • stereoelectronic control

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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