The structure-directed synthesis of cyclacene and polyacene derivatives

Ulrich Girreser, Daniele Giuffrida, Douglas Philp, J. Fraser Stoddart, Franz H. Kohnke, John P. Mathias

Research output: Contribution to journalArticlepeer-review

67 Scopus citations

Abstract

The treble diastereoselectivities exhibited by Diels-Alder reactions which occur between diene and dienophilic components associated with bicyclic systems have been employed in the stepwise construction of compounds with molecular architectures that resemble cups and cages. These macropolycyclic compounds are potential synthetic precursors of novel hydrocarbons composed of [a,d]-fused and [a,c]-fused six-membered rings. The hydrocarbons themselves are of considerable importance in investigating the behaviour of π-electrons in highly-conjugated cyclic systems and in understanding the influence upon the aromaticity and antiaromaticity of benzenoid and fused benzenoid rings that are obliged to become bent.

Original languageEnglish (US)
Pages (from-to)119-125
Number of pages7
JournalPure and Applied Chemistry
Volume65
Issue number1
DOIs
StatePublished - Jan 1 1993

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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