Literature DB >> 21879133

Claisen rearrangements of equilibrating allylic azides.

Donald Craig1, John W Harvey, Alexander G O'Brien, Andrew J P White.   

Abstract

Equilibrating mixtures of allylic azide-containing allylic alcohols or allylic 2-tolylsulfonylacetic esters undergo Johnson-Claisen or Ireland-Claisen rearrangement reactions to give unsaturated γ-azidoesters and -acids, respectively. Decarboxylation of the acids under basic conditions gives azidosulfones, with moderate to high diastereoselectivity.

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Year:  2011        PMID: 21879133     DOI: 10.1039/c1ob05972f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  8 in total

Review 1.  Allylic azides: synthesis, reactivity, and the Winstein rearrangement.

Authors:  Angela S Carlson; Joseph J Topczewski
Journal:  Org Biomol Chem       Date:  2019-05-08       Impact factor: 3.876

2.  "It's a (Kinetic) Trap!" - Selectively Differentiating Allylic Azide Isomers.

Authors:  Joseph J Topczewski; Matthew R Porter
Journal:  Synlett       Date:  2018-07       Impact factor: 2.454

3.  Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

Authors:  Matthew R Porter; Rami M Shaker; Cristian Calcanas; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2018-01-10       Impact factor: 15.419

4.  Evidence for a Sigmatropic and an Ionic Pathway in the Winstein Rearrangement.

Authors:  Amy A Ott; Mary H Packard; Manuel A Ortuño; Alayna Johnson; Victoria P Suding; Christopher J Cramer; Joseph J Topczewski
Journal:  J Org Chem       Date:  2018-06-14       Impact factor: 4.354

5.  Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.

Authors:  Ruzhang Liu; Osvaldo Gutierrez; Dean J Tantillo; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2012-04-10       Impact factor: 15.419

6.  On the Winstein rearrangement: equilibrium and mechanism.

Authors:  Amy A Ott; Joseph J Topczewski
Journal:  ARKIVOC       Date:  2019-03-30       Impact factor: 1.140

7.  A concomitant allylic azide rearrangement/intramolecular azide-alkyne cycloaddition sequence.

Authors:  Rakesh H Vekariya; Ruzhang Liu; Jeffrey Aubé
Journal:  Org Lett       Date:  2014-03-17       Impact factor: 6.005

8.  Insight into the factors controlling the equilibrium of allylic azides.

Authors:  Margarita M Vallejos; Guillermo R Labadie
Journal:  RSC Adv       Date:  2020-01-27       Impact factor: 4.036

  8 in total

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