What question did this study set out to answer?

To examine the capability of organoaluminum reagents to promote and mediate the Beckmann rearrangement of oxime sulfonates for selective synthetic transformations.

May 1, 1983Journal of the American Chemical Society

Organoaluminum-promoted Beckmann rearrangement of oxime sulfonates

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Authors

KMKeiji MaruokaUniversity of Hawaii System TMT. MiyazakiTokushima University MAMamoru Ando

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Implication

Experimental study demonstrates organoaluminum-promoted Beckmann rearrangement of oxime sulfonates, highlighting versatile strategies for carbon-nitrogen bond formation.

Key Points

To examine the capability of organoaluminum reagents to promote and mediate the Beckmann rearrangement of oxime sulfonates for selective synthetic transformations.
Treated various oxime sulfonate derivatives with organoaluminum compounds under regulated experimental conditions.
Investigated the behavior of reactive iminocarbocation intermediates toward nucleophilic alkylation and ring-formation pathways.
Organoaluminum promoters effectively triggered the Beckmann rearrangement of oxime sulfonates under mild synthetic conditions.
Facilitated tandem rearrangement and nucleophilic addition sequences, providing access to substituted amides, amines, and cyclic nitrogen scaffolds.

Cite This Study

Maruoka et al. (1983) studied this question.

synapsesocial.com/papers/69dd0af6aa9a964e8d1332be https://doi.org/10.1021/ja00347a052

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Implication

Experimental study demonstrates organoaluminum-promoted Beckmann rearrangement of oxime sulfonates, highlighting versatile strategies for carbon-nitrogen bond formation.

Organoaluminum-promoted Beckmann rearrangement of oxime sulfonates

Discussion

Member takes

Implication

Key Points

Cite This Study

Organoaluminum-promoted Beckmann rearrangement of oxime sulfonates

Discussion

Member takes

Implication

Key Points

Cite This Study

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