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Direct Preparation of Benzofurans from O-Arylhydroxylamines

Fanny Contiero, Kevin M. Jones, Edward A. Matts, Achim Porzelle, Nicholas C. O. Tomkinson*

*School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK, Email: tomkinsonnccardiff.ac.uk

F. Contiero, K. M. Jones, E. A. Matts, A. Porzelle, N. C. O. Tomkinson, Synlett, 2009, 3003-3006.

DOI: 10.1055/s-0029-1218273 (free Supporting Information)


Abstract

Reaction of O-arylhydroxylamine hydrochlorides with either cyclic or acyclic ketones in the presence of methanesulfonic acid leads directly to the benzofuran derivative via a proposed one-pot condensation-rearrangement-cyclisation reaction sequence in good to excellent yields.


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proposed mechanism



Key Words

benzofurans, hydroxylamines, sigmatropic rearrangement


ID: J60-Y2009-3300