On the non-classical course of Polonowski reactions of N-benzylmorpholine-N-oxide (NBnMO) |
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Authors: | Thomas Rosenau Peter Schmid Paul Kosma |
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Institution: | Christian-Doppler-Laboratory, Department of Chemistry, University of Natural Resources and Applied Life Sciences, A-1190 Vienna, Austria |
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Abstract: | The Polonowski reaction of NBnMO (4) afforded tropone (10) and the novel isoindole 11 besides the expected products benzaldehyde and acetmorpholide, in a temperature-dependent ratio. The reaction proceeded via two primary carbenium-iminium ion intermediates, an exo-centered species 5 which underwent a benzylium-tropylium type rearrangement, and a ring-centered species 6, which reacted further to isoindole 11 by intramolecular electrophilic substitution. The experimental findings were in good agreement with DFT computational data. |
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Keywords: | Amine N-oxides Polonowski reactions Carbenium-iminium ions Rearrangement |
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