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Issue 40, 2014
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Pyrolysis of azetidinone derivatives: a versatile route towards electron-rich alkenes, C-1 allylation and/or homologation of aldehydes

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Abstract

Pyrolysis of β-lactams and β-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-β-lactams were synthesized by the standard Staudinger ketene-imine [2 + 2] cycloaddition. The corresponding β-thiolactams have readily been obtained in good yields by thiation of β-lactams with Lawesson's reagent.

Graphical abstract: Pyrolysis of azetidinone derivatives: a versatile route towards electron-rich alkenes, C-1 allylation and/or homologation of aldehydes

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Supplementary files

Article information


Submitted
05 Feb 2014
Accepted
22 Apr 2014
First published
01 May 2014

RSC Adv., 2014,4, 21023-21031
Article type
Paper
Author version available

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

N. S. Al-Hamdan, O. M. Habib, Y. A. Ibrahim, N. A. Al-Awadi and O. M. E. El-Dusouqui, RSC Adv., 2014, 4, 21023
DOI: 10.1039/C4RA01024H

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