Synthesis of butadiyne-bridged [4n] metacyclophanes having exo-annular t-butyl groups

Yoshito Tobe*, Naoto Utsumi, Atsushi Nagano, Motohiro Sonoda, Koichiro Naemura

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Scopus citations


Butadiyne-bridged [44]- and [48]metacyclophanes having exo-annular t-butyl groups were prepared by intermolecular Eglinton coupling of the dimeric unit or by intramolecular ring closure of the linear tetramer. Comparison of the 1H and 13C NMR spectra of [44]metacyclophane with those of [48]cyclophane and diphenylbutadiyne revealed its prominent geometrical feature due to deformation of the triple bonds from linearity. The [44]Metacyclophane was converted into [08]thiophenometacyclophane in good yield by treatment with sodium sulfide.

Original languageEnglish
Pages (from-to)8075-8083
Number of pages9
Issue number38
StatePublished - 17 Sep 2001


  • Alkynes
  • Coupling reactions
  • Cyclophanes
  • Polyynes
  • Strained compounds
  • Thiophenes

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