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25.1.2.2.3 Variation 3: Oxidation with Hypervalent Iodine Reagents

DOI: 10.1055/sos-SD-025-00010

Podlech, J.Science of Synthesis, (20072538.

1,1,1-Triacetoxy-1,2-benziodoxol-3(1H)-one (16), commonly known as DessMartin periodinane (Scheme 15),[‌94‌,‌95‌] is one of the most powerful reagents for the oxidation of primary and secondary alcohols to aldehydes and ketones, respectively.[‌96‌‌98‌] A related reagent of almost equal importance as an oxidant for converting alcohols into carbonyl compounds is 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (2-iodylbenzoic acid, IBX, 17); incidentally, this compound is the precursor of DessMartin periodinane. 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (17) may be immobilized on silica gel in the form of the reagent 18, or as the polymer-bound alternative 19.[‌99‌,‌100‌]

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M8 Meeee (%) Mee
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Meeeeeeeeee 88

M8 Meeeeee, Meeeeee Meeee (%) Mee
88, MMMM 888 [‌888‌]
(MM8)8MMMeee 88, MMMM 888 [‌888‌]
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(M)-8-[(Meeeeeeeeeeeeeeee)eeeee]-8-eeeeeeeeeeeee [88, M8=MM(eMe)MMMee]; Meeeeee Meeeeeeee:[‌88‌]

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(M)-8-(eeee-Meeeeeeeeeeeeeeeeee)-8-eeeeeeeeeeeeee [88, M8=MM(Me)MM8MMMMMM]; Meeeeee Meeeeeeee:[‌888‌]

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M-(eeee-Meeeeeeeeeeeee)eeeeeeeee-8-eeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌]

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References