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Transition-Metal-Free Synthesis of Ynol Ethers and Thioynol Ethers via Displacement at sp Centers: A Revised Mechanistic Pathway

Vincent James Gray, James Cuthbertson and Jonathan D. Wilden*

*Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, U.K., Email: j.wildenucl.ac.uk

V. J. Gray, J. Cuthbertson, J. D. Wilden, J. Org. Chem., 2014, 79, 5869-5874.

DOI: 10.1021/jo500814y (free Supporting Information)


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Abstract

A wide range of ynol ethers can be prepared via displacement at an sp center. The same protocol can be applied to the synthesis of synthetically useful thioynol ethers. This reaction, which generates highly functionalized, heteroatom-substituted alkynes, involves radical intermediates.


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Key Words

ethers, sulfides


ID: J42-Y2014