Publication Details (including relevant citation information):
Al-Hamdan, Nouf S., Habib, Osama M., Ibrahim, Yehia A., Al-Awadi, Nouria A., El-Dusouqui, Osman M. E. RSC Advances 2014 4 (40) 21023-21031
Abstract: Pyrolysis of [small beta]-lactams and [small 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-[small beta]-lactams were synthesized by the standard Staudinger ketene-imine [2 + 2] cycloaddition. The corresponding [small beta]-thiolactams have readily been obtained in good yields by thiation of [small beta]-lactams with Lawesson's reagent.
Address (URL): http://dx.doi.org/10.1039/C4RA01024H