Literature DB >> 10814059

On the mechanism of the dimethyldioxirane oxidation of sigma(H) adducts (Meisenheimer complexes) generated from nitroarenes and carbanions

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Abstract

The mechanism of the novel dimethyldioxirane (DMD) oxidation of sigma(H) adducts (Meisenheimer complexes) generated from nitroarenes and carbanions was elucidated. The proposed mechanism, which is akin to that of the oxidative Nef reaction, is supported by the isolation of the cyclohexadienone intermediate and the lack of a primary kinetic isotopic effect. Protic solvents (H(2)O, MeOH) enhance the reactivity of DMD through intermolecular hydrogen bonding.

Entities:  

Year:  2000        PMID： 10814059     DOI： 10.1021/jo9915628

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  2 in total

1.  General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C-H acids in aprotic media promoted by combination of strong bases and silylating agents.

Authors:  Michał Wiȩcław; Mariusz Bobin; Andrzej Kwast; Robert Bujok; Zbigniew Wróbel; Krzysztof Wojciechowski
Journal:  Mol Divers       Date:  2015-08-11       Impact factor: 2.943

2.  Transition metal-free direct dehydrogenative arylation of activated C(sp3)-H bonds: synthetic ambit and DFT reactivity predictions.

Authors:  Kaitlyn Lovato; Lirong Guo; Qing-Long Xu; Fengting Liu; Muhammed Yousufuddin; Daniel H Ess; László Kürti; Hongyin Gao
Journal:  Chem Sci       Date:  2018-08-27       Impact factor: 9.825
  2 in total

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