Photochemical generation of the 2-azabicyclo[4.2.0]octa-4,7-diene skeleton
Tyler Fahrenhorst-Jones
A , G. Paul Savage B and Craig M. Williams A *
A School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, Qld 4072, Australia.
B CSIRO Manufacturing, Ian Wark Laboratory, Melbourne, Vic. 3168, Australia.
Australian Journal of Chemistry 75(11) 884-887 https://doi.org/10.1071/CH22139
Submitted: 16 June 2022 Accepted: 19 July 2022 Published: 31 August 2022
© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)
Abstract
A 2-azabicyclo[4.2.0]octa-4,7-diene derivative was unexpectedly isolated from the photochemical irradiation of 2-vinyl-1,2-dihydropyridine. A cascading 6π–8π–4π electrocyclic rearrangement has been proposed as a possible mechanistic pathway.
Keywords: azabicyclo[4.2.0], azaoctadiene, cascade, dihydropyridine, electrocyclisation.
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