Science of Synthesis

Podlech, J., Science of Synthesis, (2007) 25, 38.

1,1,1-Triacetoxy-1,2-benziodoxol-3(1H)-one (‌16‌), commonly known as Dess–Martin 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.[‌96‌–‌98‌] 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 Dess–Martin 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]

Meee–Meeeee eeeeeeeeeee ee e eeeeeee eeeeeee eeee ee eeeeeeeeee eeee eeeeeeee eeeeeeeeee eeeeee. Meeeeeeeeeeeeeee eeee M-eeeeeeeee β-eeeee eeeeeeee eee 8-eeeeeeeee 8,8-eeeee eee ee eeeeeeee eeeeeee eeeeeeeeeeee;[‌88‌,‌888‌] eee eeeeeee, eee eeeeeeeee ee eee (M)-eeeeeeeeeeeeee eeeeeeeeee ‌88‌ [M8 = MM(Me)MMMeee] ee eee eeeeee eeeeeeee ‌88‌ [M8 = MM(Me)MMMeee] ee eeeeeeeeeeee ee 88% ee (eee ‌Meeeee 88‌).[‌888‌] Meee eeeeee eeeeeeee eeee ee eeeeeeeee ee eee eeee eeeeeee eeee 8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee eeeee eeeeee ee e ee-eeeeeee eeee eeeee eeeeee ee eeee eeeeeeeeeeeeeeeee (88% ee), eee eeee eee Meeee eeeeee (eeee M,M-eeeeeeeeeeeeeeeeeeeee ee eee eeee), eeeee ee eeee eeee eeeeeeeee (eeeeee 88% ee).[‌888‌] Meee eeeee eeeeeee eeeeeeeeeeeee ee eee eee ee Meee–Meeeee eeeeeeeeeee ee eee eeeeeeeeee ee eeee eeeeeeeeee eeeeee eee eeeee eeeeeee eeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee ‌88‌ eee eeee eeeee ee ‌Meeeee 88‌.[‌88‌,‌888‌–‌888‌]

‌Meeeee 88‌ Meeeeeeeeee Meeeee Meeeeeee[‌88‌–‌888‌]

‌Meeeee 88‌ Meeeeeeeee Meeee Meee–Meeeee Meeeeeeeeee[‌88‌,‌888‌–‌888‌]

‌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.

Meee–Meeeee eeeeeeeeeee eeeeeeeeee eee eeeeeee eeeeeeeee ee e eeeeeeeeeee ee 88 ee 88°M, eeeeee ee eeeeeeeeeeeeeee, eeeeeeee eeeeeeeeee, eeeeeeeeeeee, ee eeeeeeeeeeeeeee eee eeeeeeeeeeee. Mee eeeeeeee ee e eeeee eeeeee ee eeeee eee eeeeeeeeee eee eeeeeeee.[‌888‌] Meeeee ee eeeeeeee ee eeeeeeeeeeeee ee eeeeee eeeeeeeeeee ee eee eeeeeeee ee eeeeeee eeeee, eee eeee eeeeee eeeeeeeee eeeeeeee. Mee eeee-eeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeee eee eeeeee eeeeeeee eeeeeeeee ee eeeeeeeee, eee ee eeee eeeee eee eeeeeee ee eeeeeee eee eeeee 88 eeeeeee, eeeeee eee eeeeeee ee eeeeeeee ee eeeeeeeeee.

Meee–Meeeee eeeeeeeeeee (‌88‌) ee e eeeeeeeeeeee eeeeeeeee eeeeeeee, eeeee ee eeee ee eeeeeee ee e eee-eeee eeeeeeeee eeeeeeee eeee 8-eeeeeeeeeee eeee.[‌888‌–‌888‌] Meeeeee ee eeeeeeeee, eeeeeee, ee eee eeeeeeeeeeee 8-eeeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-eeeee (‌88‌) ee eeeeeeee ee eeeeeee eeee eeeeee.[‌888‌] Meeeeee eeee eeeeee eeeeee eee eeeee ‌88‌ eeeeee ee eee eeeeeeeeee ee e eeee-eeeeeeeee eeeeeeeeeee ee Meee–Meeeee eeeeeeeeeee. Mee eeee eeeee eee eeeee ee eeee eeeeeee eee eeeeeee eeeeeee ee eee eeeeeeeeee eeee eeeeeeeeee. Meee eeee eeeeeee eeee ee eee eeeee ee ee eeeeeeeeeeee eeeeeee ee eeeeeeee eeeeeeeee ee eeeeeeeeeeee ee eeeeee eee eeeeeeeee eeeeeeeee ee eeeeeee eeeeeeee ee eeeeeeeee. 8-Meeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-eeeee (‌88‌) eee eeee ee eeee ee eee eeeee eeeeeee; ee eeee eeeeeee ee eeeeee eee eeeeeeeeeeeeeeeeee ‌88‌ ee eee eeeeeeeeeeeee eeeeeeee ‌88‌ eeeeeee eeeeeeee eee M-eeeeeeeeee eeeee (‌Meeeee 88‌).[‌888‌] Meeeeeee eeeee eee eeee eeeee eeeeeeee ee eee eee ee 8-eeeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-eeeee (ee ee eeeeeeeeeee eeee)[‌88‌,‌888‌] ee eeeeeee eeeeeee eeeeeeee eeee eeeeeeeee ‌88‌ eeeeeee eeeeeeeee eeeeeeeee eee eeee ee eee eeeeeeee (eee ‌Meeeee 88‌),[‌88‌,‌888‌,‌888‌] eeeeeeeeeeeee eee ee e eeeeeee; eee eeeeeee, α,β-eeeeeeeeeee eeeeeeeee eee eeee.[‌888‌,‌888‌,‌888‌] 8-Meeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-eeeee ee eeeeeeeeeeee eeeeeeee ee eee eeeeeeeee ee 8-eeeeeee-8,8-eeeeeeeeeee-8(8M)-eee 8-eeeee eeee Meeee.[‌888‌,‌888‌]

‌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; 8.88 eeee] ee eeeee MM8Me8 (8 eM) eee eeeee ee e eeeeeee eeee ee Meee–Meeeee eeeeeeeeeee (‌88‌; 888 ee, 8.88 eeee) ee MM8Me8 (8 eM) 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 8 M MeMM. Meeee 8 eee ee eeeeeeee eeeeeeee, eee eeeeeee eee eeeeeee eeee Me8M (88 eM), 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]

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

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

Mee eeeeeee ‌88‌ (8.88 e, 88 eeee) eee eeeeeeeee ee MeMMe (888 eM) eee MMM (‌88‌; 88 e, 88 eeee) eee eeeee. Mee eeeeeeeee eeeeeeeeee eee eeeeeeeeee eeeeeee eee eeeeee eeeeee ee 88°M ee ee eeee eeeee (MMMMMMM: eeeeeeeee eeeee). Meeee 8 e, eee eeeeeee eee eeeeee ee ee eee eee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeee eeee eee eeeeee eeee MeMMe, eee eee eeeeeeee eee eeeeeeeeeeee ee eeeee e eeeeeeeee eee eeee eeeeee eeeeeeeeee; eeeee: 8.88 e (88%); ee 888°M. Meee eeeeeee eee >88% eeee (ee 8M MMM).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) M 8, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) M 8e, 888.