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Short Paper | Regular issue | Vol 91, No. 1, 2015, pp.149-156
Published online, 7th January, 2015
DOI: 10.3987/COM-14-13131
Further Investigation of Pyranone Activation

Justin A. Simanis, Christian R. Zwick, Erica L. Woodall, John R. Goodell, and T. Andrew Mitchell*

*Campus Box 4160, Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, U.S.A.

Abstract

As part of our ongoing investigation into the activation parameters of pyranones to the corresponding oxidopyryliums, various means were investigated. Screening of acid mediators revealed limited efficiency, with HCl providing the best result. Additional acid-mediated and microwave-assisted studies provided evidence that oxocarbenium formation is a key mechanistic event thwarting formation of oxidopyrylium intermediates. A µW-assisted exchange process was discovered allowing for the rapid synthesis of potentially useful alkoxypyranones.