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Evidence for the Intermediacy of Arylbenzylnitrenium Ions in the Thermal Rearrangement of Isoxazolidines Derived from C,N-Diarylnitrones and 2-Morpholin-4-yl-acrylonitrile

✍ Scribed by Annie Liard; Thi-Huu Nguyen; Abdel Illah Djelloul Smir; Michel Vaultier; Aïcha Derdour; Jacques Mortier


Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
179 KB
Volume
9
Category
Article
ISSN
0947-6539

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✦ Synopsis


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.