Synthesis of cis,cis,cis,cis-[5.5.5.4]-1-azafenestrane with discovery of an unexpected dyotropic rearrangement

Scott E Denmark, Justin I. Montgomery

Research output: Contribution to journalArticle

Abstract

(Figure Presented) An unprecedented skeletal reorganization initially hindered a concise route based on a tandem [4+2]/[3+2] nitroalkene cycloaddition for the synthesis of the strained title compound. Conditions to suppress the observed dyotropic rearrangement were developed, and X-ray crystallographic analysis of the BF3 derivative (see picture) of the azafenestrane revealed significant planarization around the central carbon atom.

Original languageEnglish (US)
Pages (from-to)3732-3736
Number of pages5
JournalAngewandte Chemie - International Edition
Volume44
Issue number24
DOIs
StatePublished - Jun 13 2005

Keywords

  • Cycloaddition
  • Dyotropic rearrangement
  • Fenestranes
  • Nitroalkenes
  • Strained molecules

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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