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Improved Procedure for the Synthesis of Enamine N-Oxides

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journal contribution
posted on 06.06.2008 by David Bernier, Alexander J. Blake, Simon Woodward
An improved procedure for the preparation of enamine N-oxides involving aminolysis of epoxides, chlorination, N-oxidation, and dehydrochlorination is described. Although isolated β-chloroamine N-oxides are prone to rearrangements when isolated, these side reactions can be slowed by the presence of stabilizing organic acids. The scope and limitations of this strategy are discussed.