Issue 0, 1987

Selective ortho-alkylation of phenols with sulphoxides via[2,3]sigmatropic rearrangement: synthesis of coumarins

Abstract

ortho-Alkylphenols have been prepared from phenol and dialkyl sulphoxides via[2,3]sigmatropic rearrangement, using thionyl chloride or phenyl chlorosulphinate as an activator of sulphoxides. In the same manner, ortho-phenylthiomethylphenol has been prepared in good yield. When ethyl phenyl sulphoxide, diallyl sulphoxide, and methyl methylsulphinylacetate were used as sulphoxides, none of the expected products were obtained. Salicylaldehyde has been prepared in moderate yield, when methyl methylthiomethyl sulphoxide was used as a sulphoxide. 3-(2-Hydroxyphenyl)propionic acid derivatives, which were obtained from substituted phenols and dimethyl 3,3′-sulphinyldipropionate, have been cyclized to give the corresponding coumarins in good yields.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1987, 1753-1756

Selective ortho-alkylation of phenols with sulphoxides via[2,3]sigmatropic rearrangement: synthesis of coumarins

K. Sato, S. Inoue, K. Ozawa, T. Kobayashi, T. Ota and M. Tazaki, J. Chem. Soc., Perkin Trans. 1, 1987, 1753 DOI: 10.1039/P19870001753

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements