Literature DB >> 26225452

Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones with Hypervalent Iodine Reagents.

Camilla Matassini1, Camilla Parmeggiani1,2, Francesca Cardona1, Andrea Goti1.   

Abstract

Hypervalent iodine compounds are viable reagents for the oxidation of N,N-disubstituted hydroxylamines to the corresponding nitrones, with IBX performing best. The procedure is very simple and user-friendly and affords the target compounds with high efficiency and regioselectivity, highlighting IBX as the reagent of choice for preparation of aldonitrones from nonsymmetric hydroxylamines. Evidence for a mechanism involving nitrogen to iodine coordination has been collected.

Entities:  

Year:  2015        PMID： 26225452     DOI： 10.1021/acs.orglett.5b02029

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Synthesis of (±)-Setigerumine I: Biosynthetic Origins of the Elusive Racemic Papaveraceae Isoxazolidine Alkaloids*.

Authors:  Ana V Serna; László Kürti; Juha H Siitonen
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-18       Impact factor: 15.336

2.  Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.

Authors:  Vladislav G Lisnyak; Tessa Lynch-Colameta; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-19       Impact factor: 15.336

3.  1-Oxo-2,2,6,6-tetramethylpiperidinium bromide converts α-H N,N-dialkylhydroxylamines to nitrones via a two-electron oxidation mechanism.

Authors:  Anastas D Stoyanovsky; Detcho A Stoyanovsky
Journal:  Sci Rep       Date:  2018-10-17       Impact factor: 4.379
  3 in total

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