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(Cyclopentadienone)iron-Catalyzed Transfer Dehydrogenation of Symmetrical and Unsymmetrical Diols to Lactones

Yidan Tang, Rowan I. L. Meador, Casina T. Malinchak, Emily E. Harrison, Kimberly A. McCaskey, Melanie C. Hempel and Timothy W. Funk*

*Department of Chemistry, Gettysburg College, Gettysburg, Pennsylvania 17325, United States, Email: tfunkgettysburg.edu

Y. Tang, R. I. L. Meador, C. T. Malinchak, E. E. Harrison, K. A. McCaskey, M. C. Hempel, T. W. Funk, J. Org. Chem., 2020, 85, 1823-1834.

DOI: 10.1021/acs.joc.9b01884 (free Supporting Information)



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Abstract

Air-stable iron carbonyl compounds bearing cyclopentadienone ligands with TMS groups in the 2- and 5-positions catalyze dehydrogenative diol lactonization reactions using acetone as both the solvent and hydrogen acceptor. Lactones containing five-, six-, and seven-membered rings were successfully synthesized, and no over-oxidations to carboxylic acids were detected.

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Key Words

lactones, acetone


ID: J42-Y2020