Literature DB >> 23897657

Structures and ambident reactivities of azolium enolates.

Biplab Maji1, Herbert Mayr.   

Abstract

Oxygen versus carbon: Azolium enolates were generated by the reactions of N-heterocyclic carbenes (NHCs) with methyl phenyl ketene and characterized by X-ray crystallography. Kinetic studies show that the enolate oxygen is 20 times more nucleophilic than the carbon atom, but under thermodynamic control exclusive C-addition products were formed.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocyclic carbenes; acylazolium ions; kinetics; nucleophilicity; zwitterions

Year:  2013        PMID: 23897657     DOI: 10.1002/anie.201303524

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  1 in total

1.  Competition between N and O: use of diazine N-oxides as a test case for the Marcus theory rationale for ambident reactivity.

Authors:  Kevin J Sheehy; Lorraine M Bateman; Niko T Flosbach; Martin Breugst; Peter A Byrne
Journal:  Chem Sci       Date:  2020-07-23       Impact factor: 9.825

  1 in total

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