Evidence for the intermediacy of arylbenzylnitrenium ions in the thermal rearrangement of isoxazolidines derived from C,N-diarylnitrones and 2-morpholin-4-yl-acrylonitrile.
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.
Liard
Annie
A
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.
Nguyen
Thi-Huu
TH
Djelloul Smir
Abdel Illah
AI
Vaultier
Michel
M
Derdour
Aïcha
A
Mortier
Jacques
J