Bicyclic imides with bridgehead nitrogen. synthesis and x-ray crystal structure of a bicyclic 2,4-oxazolidinedione1

Academic Article


  • The first successful synthesis of bicyclic 2,4-oxazolidinediones with bridgehead nitrogen, examples of anti-Bredt imides, was accomplished. The synthetic approaches involved three homologous bridging sizes, and the smallest product capable of preparation was l-aza-8,9-dioxo-7-oxa-6-phenylbicyclo[4.2.1]nonane, for which the structure was verified by X-ray diffraction. Also prepared was l-aza-9,10-dioxo-8-oxa-7-phenylbicyclo[5.2.1]decane. These results were accurately predicted by using anti-Bredt olefins as models, suggesting that resonance effects may be essential for the stability of anti-Bredt imides. © 1984, American Chemical Society. All rights reserved.
  • Published In

    Digital Object Identifier (doi)

    Pubmed Id

  • 14983006
  • Author List

  • Brouillette WJ; Einspahr HM
  • Start Page

  • 5113
  • End Page

  • 5116
  • Volume

  • 49
  • Issue

  • 26