Monatshefte für Chemie / Chemical Monthly

, Volume 133, Issue 4, pp 485–497 | Cite as

Photochemical Transformation of Levoglucosan Imides to Anhydrosugar-Annelated Azepanediones and Azocanediones

  • Christian Sund
  • Swantje Thiering
  • Joachim Thiem
  • Jürgen Kopf
  • Markus Stark

Summary.

 By reaction of O-protected 3-amino-1,6-anhydro-β-D-glucopyranose with succinic, glutaric, and tartaric anhydride, respectively, the corresponding 3-substituted succinimido, glutarimido, and tatarimido derivatives were obtained. Irradiation of the succinimido and glutarimido derivatives at 254 nm gave 1,4-diradical intermediates by γ-hydrogen abstraction (Norrish Type II reaction) which subsequently recombined (Yang cyclization) to form azetidinols. These in turn fragmented and led to azepanedione and azocanedione derivatives. In contrast, irradiation of the tartarimido derivative resulted in elimination and led to both isomeric enolethers.

Keywords. 1 6-Anhydroglucopyranose; Photochemistry; Intramolecular alkylation; Anhydrosugar-annelated azepanediones and azocanediones. 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Copyright information

© Springer-Verlag/Wien 2002

Authors and Affiliations

  • Christian Sund
    • 1
  • Swantje Thiering
    • 1
  • Joachim Thiem
    • 1
  • Jürgen Kopf
    • 2
  • Markus Stark
    • 3
  1. 1. Institute of Organic Chemistry, University of Hamburg, D-20146 Hamburg, GermanyDE
  2. 2. Institute of Inorganic Chemistry, University of Hamburg, D-20146 Hamburg, GermanyDE
  3. 3. Bell Flavors and Fragrances, Duft und Aroma GmbH, D-04205 Leipzig, GermanyDE

Personalised recommendations