The Claisen rearrangement of 2-phenylsulfinyl-2-propenyl phenyl ethers –A new route to functionalized phenols and 2-methylbenzofurans

KHAN, Akram (1991). The Claisen rearrangement of 2-phenylsulfinyl-2-propenyl phenyl ethers –A new route to functionalized phenols and 2-methylbenzofurans. Bulletin of the chemical society of Japan, 64 (12), 3682-3686.

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Official URL: https://www.journal.csj.jp/doi/fpi/10.1246/bcsj.64...
Link to published version:: https://doi.org/10.1246/bcsj.64.3682

Abstract

The hitherto unknown Claisen rearrangement of 2-phenylsulfinyl-2-propenyl phenyl ethers to the corresponding 2-(2-phenylsulfinyl-2-propenyl)phenols is reported. The latter compounds underwent Michael reactions with a variety of nucleophiles to provide functionalized phenolic adducts. O-Alkylation of the initial rearrangement products with 3-bromo-2-phenylsulfinyl-1-propene and 2,3-dibromo-l-propene followed by [3,3] sigmatropic rearrangement provided a promising route to 7-substituted 2-methylbenzofurans.

Item Type: Article
Departments - Does NOT include content added after October 2018: Health and Well-being > Department of Bioscience
Identification Number: https://doi.org/10.1246/bcsj.64.3682
Depositing User: Louise Beirne
Date Deposited: 20 Sep 2018 12:31
Last Modified: 20 Sep 2018 12:31
URI: http://shura.shu.ac.uk/id/eprint/22610

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