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

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.