Evidence for the trapping of a non-Kekulé intermediate in the photoretro-aldol type reaction of m-nitrobenzyl derivatives
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 19,p. 1426-1428
- https://doi.org/10.1039/c39890001426
Abstract
The acid-catalysed photoretro-aldol type reaction of m-nitro-substituted derivatives was found to give 3-(N-3′-nitrobenzyl-N-hydroxyamino)benzyl alcohol (4) as the only product derived from the nitrobenzyl fragment; the structure of (4) has been determined by X-ray crystallography and the mechanism for its formation requires the intermediacy of a non-Kekulé intermediate in which direct transmission of charge between the 1,3-positions of the benzene ring occurs.Keywords
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