The meisenheimer transformation of (+)-nupharidine

LaLonde, Robert T.; Woolever, John T.; Auer, Egmont; Wong, C. F.

doi:10.1016/s0040-4039(01)84668-2

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2010

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Cited by 6 publications

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Meisenheimer Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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The tertiary aliphatic amine oxides (tertiary N ‐oxides) undergo to thermal transformation into substituted N ‐alkoxylamines or N ‐hydroxylamines, and generally referred to as the Meisenheimer rearrangement. The study finds that this reaction takes place through a radical mechanism involving a homolytic cleavage of a nitrogen‐carbon bond and the migration of an alkyl group to form the N ‐alkoxylamine. This rearrangement does not apply to aromatic N ‐oxides. The reaction mechanism for such rearrangement has been discussed for aryl allyl N ‐oxides, N ‐propargylmorpholine N ‐oxide and N ‐propargylmorpholine N ‐oxide. This reaction has been found to be useful for organic synthesis.

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