Evidence for the intermediacy of arylbenzylnitrenium ions in the thermal rearrangement of isoxazolidines derived from C,N-diarylnitrones and 2-morpholin-4-yl-acrylonitrile |
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| Authors: | Liard Annie Nguyen Thi-Huu Djelloul Smir Abdel Illah Vaultier Michel Derdour Aïcha Mortier Jacques |
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| Institution: | Unité de chimie organique moléculaire et macromoléculaire, Université du Maine, UMR CNRS 6011, Faculté des sciences et techniques, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France. |
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| Abstract: | In contrast to the diaryl, dialkyl, alkylaryl, and parent series, nothing is known about the generation and chemical behavior of arylbenzylnitrenium ions. Herein, we report that these species can be generated by a process involving an unprecedented thermal rearrangement of isoxazolidines derived from C,N-diarylnitrones and 2-morpholin-4-yl-acrylonitrile. The products from these reactions are dramatically dependent upon the nature of the nitrone. Most of the observed chemistry originates from the singlet state. |
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| Keywords: | alkenes captodative alkenes electrophilic reactions nitrenium ions rearrangement |
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