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Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones

Benoit Basdevant and Claude Y. Legault*

*Université of Sherbrooke, CCVC, Department of Chemistry, 2500 Boul. de l’Université, Sherbrooke, Québec J1K 2R1, Canada, Email: claude.legaultusherbrooke.ca

B. Basdevant, C. Y. Legault, J. Org. Chem., 2015, 80, 6897-6902.

DOI: 10.1021/acs.joc.5b00948 (free Supporting Information)


 

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Abstract

Enol esters were rapidly converted in high yields to their corresponding α-tosyloxy ketones in the presence of [hydroxy(tosyloxy)iodo]benzene (HTIB). Aromatic, aliphatic, and cyclic enol esters were found to be suitable substrates for the reaction.

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Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Access to α-Halo Ketones by a Release-and-Catch Mechanism

A. Jobin-Des Lauriers, C. Y. Legault, Org. Lett., 2016, 18, 108-111.


Key Words

Koser's Reagent, α-hydroxylation


ID: J42-Y2015