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Please login to access the full content or check if you have access via Variation 7: By Oxidation with Hydroxy(mesyloxy)iodobenzene

DOI: 10.1055/sos-SD-026-00761

Suffert, J.Science of Synthesis, (200526939.

Hydroxy(mesyloxy)iodobenzene oxidizes aliphatic ketones and affords the mesyloxylated derivatives 221.[‌191‌] Yields are good, and the reactions proceed under reflux in acetonitrile; they may involve an enolic intermediate such as 220. Although the α-mesyloxylation of 1-cyclopropylethanone with this reagent is regiospecific and affords 222 in ~100% yield, such precision is not generally observed. Thus, when butan-2-one is oxidized in acetonitrile a 5:4 mixture of the isomers 223 and 224 is obtained (Scheme 101).[‌191‌]

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