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Al-Hamdan, Nouf S. [Author]; Habib, Osama M. [Author]; Ibrahim, Yehia A. [Author]; Al-Awadi, Nouria A. [Author]; El-Dusouqui, Osman M. E. [Author]

Pyrolysis of azetidinone derivatives: a versatile route towards electron-rich alkenes, C-1 allylation and/or homologation of aldehydes - [published Version]

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  • Media type: Text; E-Article
  • Title: Pyrolysis of azetidinone derivatives: a versatile route towards electron-rich alkenes, C-1 allylation and/or homologation of aldehydes
  • Contributor: Al-Hamdan, Nouf S. [Author]; Habib, Osama M. [Author]; Ibrahim, Yehia A. [Author]; Al-Awadi, Nouria A. [Author]; El-Dusouqui, Osman M. E. [Author]
  • imprint: Cambridge : Royal Society of Chemistry, 2014-05-01
  • Published in: RSC Advances 4 (2014), Nr. 40
  • Issue: published Version
  • Language: English
  • DOI: https://doi.org/10.15488/113; https://doi.org/10.1039/c4ra01024h
  • ISSN: 2046-2069
  • Keywords: Beta-Lactam Derivatives ; Flash Vacuum Thermolysis ; Macrocrocyclic Bisazetidinones ; Rcm Approach ; Thermal-Decomposition ; Ketene-Imine Cycloaddition ; Nitrogen Atom ; 4 Membered Rings ; Vinyl Ethers ; Staudinger Reaction
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  • Description: Pyrolysis of beta-lactams and beta-thiolactams led essentially to stereoselective synthesis of the high energy electron-rich Z-alkenes. Extension of this methodology to the pyrolysis of 3-allyloxy derivatives gave a simple direct route to the synthetically important 4-pentenal. These pyrolytic transformations convert aldehydes to aryloxyalkenes (a protected homologation) and 4-pentenal (a C-1 allylation and homologation). The starting 3-aryloxy and 3-allyloxy-beta-lactams were synthesized by the standard Staudinger ketene-imine [2 + 2] cycloaddition. The corresponding beta-thiolactams have readily been obtained in good yields by thiation of beta-lactams with Lawesson's reagent. ; University of Kuwait/SC 02/11 ; GF-S/GS01/01, GS02/01, GS01/03, GS01/05
  • Access State: Open Access