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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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Meeeee 88 Meeeeeeeee Meeee MeeeMeeeee Meeeeeeeeee[‌88‌,‌888‌‌888‌]

Meeeeeeeeee 88

M8 Meeee (%) Mee
88e [‌888‌]
88 [‌888‌]
888 [‌888‌]
88 [‌888‌]
888 [‌88‌]
88 [‌888‌]

e Mee MM8Me8 eee eeee ee eee eeeeeee.

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Meeeee 88 Meeeeeeee ee 8-[(M-eeee-Meeeeeeeeeeeee)eeeeeeeee-8-ee]eeeeeee eeee 8-Meeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-Meeee[‌888‌]

Meeeee 88 Meeeeee Meeeeeeeee ee Meeeeee Meeeeeee Meeee 8-Meeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-Meeee[‌88‌,‌888‌,‌888‌]

Meeeeeeeeee 88

M8 Meeeeee, Meeeeee Meeee (%) Mee
88, MMMM 888 [‌888‌]
(MM8)8MMMeee 88, MMMM 888 [‌888‌]
88, MeMM 88 [‌888‌]
88, MeMM 88 [‌888‌]
(MM8)8Me 88, MMM 88e [‌88‌]

e Meeee eeeeeeeeee ee MM/MM.

Meeeeeeeeeee Meeeeeeee

(M)-8-[(Meeeeeeeeeeeeeeee)eeeee]-8-eeeeeeeeeeeee [88, M8=MM(eMe)MMMee]; Meeeeee Meeeeeeee:[‌88‌]

Mee M-eeeeee ee eee eeeeeee 88 [M8=MM(eMe)MMMee; 8.88eeee] ee eeeee MM8Me8 (8eM) eee eeeee ee e eeeeeee eeee ee MeeeMeeeee eeeeeeeeeee (88; 888ee, 8.88eeee) ee MM8Me8 (8eM) ee 8°M, eee eeee eee eeeeeee eee eeeeeee ee eeee ee ee. Mee eeeeeeee ee eeee ee eee eeeeeee eee ee eeeeeeeee (eeeeeeeeee ee MMM). Meee eee eeeeeeee eee eeeeeeee, eeeeee eeeeeee eee eeeeeeeee ee eee eeeeeeee ee 8M MeMM. Meeee 8eee ee eeeeeeee eeeeeeee, eee eeeeeee eee eeeeeee eeee Me8M (88eM), eee eeeeeee eeeee eee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8×). Mee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee; eeeee: eeeee.

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

MeeeMeeeee eeeeeeeeeee (88; 888e, 888eeee) eee eeeeeeeee ee MM8Me8 (888eM) eee eee M-eeeeee ee eee eeeeeee 88 [M8=MM(Me)MM8MMMMMM; 88.8e, 888eeee] eee eeeee ee 8°M. Mee eeeeeee eee eeeeeee eee 8e, eee eeee eeeeeeee eeeeeee e eee ee Me8MM8, eeeee ee eeeeeee ee eee eeeeeee; eeeee: 88.8e (88%).

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

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