Synthesis of cis,cis,cis,cis-[5.5.5.5]-1-Azafenestrane

Scott E. Denmark, Laurenz A. Kramps, Justin I. Montgomery

Research output: Contribution to journalArticlepeer-review

Abstract

To provide an opportunity for X-ray analysis of an unsubstituted fenestrane, one of the ring-fusion carbon atoms was replaced with a nitrogen atom to facilitate salt formation; the key strategic step to the first 1-azafenestrane (see scheme) involves the tandem [4+2]/[3+2] cycloaddition of a nitrocyclopentene with butyl vinyl ether. The adduct with borane provided crystals suitable for X-ray analysis, which revealed the planar deformation of the central carbon atom to be modest (116.1 and 116.6°).

Original languageEnglish (US)
Pages (from-to)4122-4125
Number of pages4
JournalAngewandte Chemie - International Edition
Volume41
Issue number21
DOIs
StatePublished - Nov 4 2002

Keywords

  • Anti-van't Hoff/Le Bel compounds
  • Cycloaddition
  • Fenestrane
  • Nitroalkene
  • Polycycles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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