Issue 26, 2017

A coherent study on the Z-enoate assisted Meyer–Schuster rearrangement

Abstract

A systematic study has been performed on the Z-enoate assisted Meyer–Schuster rearrangement of propargylic alcohols. The impact of various factors such as temperature, solvent, concentration of a counter ion of an acid, and the nature of the arene nucleophile was studied. The relative nucleophilicity of various arenes estimated in this study is in good agreement with that of Herbert Mayr's nucleophilicity scale.

Graphical abstract: A coherent study on the Z-enoate assisted Meyer–Schuster rearrangement

Supplementary files

Article information

Article type
Paper
Submitted
18 May 2017
Accepted
13 Jun 2017
First published
13 Jun 2017

Org. Biomol. Chem., 2017,15, 5579-5584

A coherent study on the Z-enoate assisted Meyer–Schuster rearrangement

P. Tharra and B. Baire, Org. Biomol. Chem., 2017, 15, 5579 DOI: 10.1039/C7OB01221G

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