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33.4.11.1.3 Methods 3: Miscellaneous Methods

DOI: 10.1055/sos-SD-033-00579

Collier, S. J.Science of Synthesis, (200733500.

N-Alk-1-enylhydroxylamines can also be prepared by less general methods, which are briefly discussed here. Because of the smaller range of applicability of these methods, experimental conditions are not given. As mentioned above, nitrones are isomeric with N-alk-1-enylhydroxylamines and can be converted into N-alk-1-enylhydroxylamines under certain conditions. For example, nitrones can be O-acylated to give the isomeric O-acyl-N-alk-1-enylhydroxylamines,[‌37‌] although the resulting products can be unstable and prone to rearrangement to α-acyloxyimines. The oxidation of nitrones can give N-alk-1-enylhydroxylamines through dimerization of the intermediate vinylaminyloxide radicals.[‌34‌,‌38‌‌40‌] In some cases the reaction is reversible, regenerating the vinylaminyloxides.[‌39‌]

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