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26.1.1.2.5.6 Variation 6: With Organic Iodine(V) Compounds

DOI: 10.1055/sos-SD-026-00003

von Angerer, S.Science of Synthesis, (20052668.

Hypervalent iodine compounds, with iodine(V) linked to a benzene ring and complexed by a carboxylate group, play an important role in the oxidation of alcohols. The most widely used reagents are the cyclic tautomer of 2-iodylbenzoic acid [IBX, 1-hydroxy-1λ3,2-benziodoxol-3(1H)-one 1-oxide; 75], which suffers from poor solubility in organic solvents, and the more soluble DessMartin periodinane (DMP; 76) (Scheme 49).[‌206‌‌208‌] These and other derivatives including those linked to solid support, and their use for the oxidation of alcohols have been reviewed.[‌3‌]

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8-Meeeeeeeeeee eeee (88) eee ee eeeeeeee eeee 8-eeeeeeeeeee eeee ee eeeeeeeee eeee eeeeeeeee eeeeeee ee eeeeeee eeeeeeee eeee, ee eeee eeeeeeeeeeee eeee Meeee (Meeeee 88).[‌888‌] Me eeeeee eee eeeeeee eeeeeeee eeeeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeee, eeee ee eee eeeeeeee ee eeeee eee-eeeeeee eeeeeeeeee eeeeee eeee ee eeeee eeeeee, eeeee eeeeee, eeeeeee, eeeeeee, eeeeeeeeee, eee eeeeee, ee eeeeeeee eeeeeeeee eeeee ee ee e eeeeeee eeee eeeeeeeeeeeeeee.[‌888‌,‌888‌]

Mee eeeeeeeee ee 8,8-eeeee eee ee eeeeeeeeee ee eeeeeee α-eeeeeeeeeeeeee eee 8,8-eeeeee, eeeeeeeeeeee, eeeeeee eeeeeeeee eeeeeeee ee eee eeeeee MM eeee.[‌888‌] 8-Meeeeeeeeeee eeee (88) eeeeeeee e eeee eeeeee ee eeeeeeeeeeeeeeee eee eee eeeeeeeee ee eeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeee eeeeee; ee eeee eee eee eeeeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeeee eeeeeeee ee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee eeee eeee ee eeeeee.[‌888‌] Me eeeeeee ee eee eeeeeeee ee eeeeeeeeeeeee eeee 8-eeeeeeeeeeee eeee (88).[‌888‌] Meeeeeeee ee eee eeeeeeee eeeeeeeeee eeeeeeeeeeeeee (88), eeeeeeeee-8-ee-8-eee (88), ee eeeeeeeeee-8,8-eeee-8-eee (88) eee eeeeee (Meeeee 88).

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeee eeee 8-Meeeeeeeeeee Meee ee Meeeeeeeeeeeee eee Mee Meeeeeeeeee Meeeeeeeeee[‌888‌]

MeeeMeeeee eeeeeeeeeee (88), eeeee ee eeeeeeeeeeee eeeeeeeee, ee eeeeee eeee eee eee eeeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeeee eeeeeeeee eeeeeeeeee eeeeee[‌888‌,‌888‌] eeeeeeeee eeeeeeeeeeeeeee eeeeee.[‌888‌] M eeeee eeeeee ee eeeee 8-eeeeee-8-eeeeeee eeeeeeeeeeee eeee eeee eeeeeeee eeee eeee eeeeeee ee eeee eee eeeeeeeeeeeee β-eeeeeeeeeeeeeee ee eeee eeeee (Meeeee 88).[888]

Meeeee 88 Meeeeeeee ee α-Meeeee Meeeeeee eeee MeeeMeeeee Meeeeeeeeee[888]

M eeeeeeeeeeeeee eeeeeeeeee eeeeeee 8-eeeeeeeeeeee eeee (88) eee MeeeMeeeee eeeeeeeeeee (88) ee eeeeeeee ee eee eeeeeeeee ee 8,8-eeeee, eeeee eeeee ee eee eeeeeeee ee eee ­eeeeee MM eeee ee eee eeeeee eeeeeee. M eeeeee eee eeeeeeeee eeeeee eee eeeeeeeeeeee eeeeeeeeee eee eeeeee eeeeeee eeee eeeeeeee, eeeee e eeeeeeeeeee eeeee, eee eeee eeeeeeeee eee eeeeeee ee eee eeeeeeeee eeeeeeeee ee eeeeeee eeeeeeee.[‌888‌]

Me eeeee ee eeeeeee e eeeeee eeeeeeee eeeeee eee eeeeeeeee eeeeeeeee ee eee eeeeeee, eeeeeee eeeeeee eeeeeeeee 8-eeeeeeeeeeee eeee eeeeeeeeeee eeee eeee eeeeeeeeeee eee eeee eee eee eeeeeeeee ee eeeeeeee; eee eeeeeeee eee eeeee ee Meeeee 88.[‌888‌,‌888‌] Meeeeeeee, eee eeeeee ee eeeeeee eeeeeeee eeee eeeee eeeeeeee eee eeee ee eeeeeeeee. MeeeMeeeee ­eeeeeeeeeee eeeeeeee ee eeeeee eee eeeeeee eeeeeeee eeeeeeee eeee eeeeeeee ee eeeeeeeee eeeeeeeeeee eeeee eeeeeee-eeee eeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeee ee 8-Meeeeeeeeeee Meee ee Meeeee Mee eee Meeeeeeeee Meeee[‌888‌,‌888‌]

Meeee 8-eeeeeeeeeeee eeee (88) eee MeeeMeeeee eeeeeeeeeee (88) eeee eeeeeeeee eeeeeeeeee eeeeeeee ee eeeeeeeee eee eeeeeeeeeeeeeee eeeeee eeeeeeee, eee eeeee eeeeeeee eeee ­eeeeeeeeeeee eeeeeeeee eeeeeeeeee eeee eeee eeeeeeeeeeee. Meeeeeeeee eeeee eeeeeee eeee ee 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee eeeeee ee ee eeeeeeeeeee eee eeee eeeeeee, ee eeeee ee eee eeeeeeeeee ee eeeeeee eeee eeeeeeee (88) (Meeeee 88). M eeeee eeeeee ee eeeeeeeee eeeeeeeee eeee 8-eeeeeeeeeeee eeee (88) eee MeeeMeeeee eeeeeeeeeee (88) eeee eeee eeeeeeeee ee eeeee eeeeeeee eeee eeeeeeeee eeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeee ee Meeeeeee eeee Meeeeee ee Meeeeeeee eeee Meee-Meeeee Meeeeeeeeee ee ee Meeee Meeeee[‌888‌]

Mee eeeeeeeee ee 8-eeeeeeeeeeee eeee (88) eee eeee eeeeeeee ee eeeeeee eeee ee eeeeeee eee eeeeeeeeee eee eeeeeeeee ee eee eeeeeee, eee ee eeeeeeee eee eeeeeeeee eeeeeeeee ee eee eeeeeeeeeee eeeeee. Me eee ee eeeee eeeeeeeeeeeee eee eeeeeeee eeeee eee eeee ­eeeeeeee eeee eee eeeeeeeeeeeeee eeeeeeeeeeee.[‌888‌] Meeeeee eeeeeeeee eeeeee, eeeeeee ee 8-eeeeeeeeeeee eeee (88), ee eeeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eee­eeeeeeeeeeeee eeee, eeeee eeeeeeee 8α-eeeeeee eeeeeeee eeeeeeee eeee eee eeeeeeeeeeeee 8,8-eeee-8-eee eeeeeeeeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee 88, 88, eee 88 ee Meeeeeeee eeee 8-Meeeeeeeeeee Meee (88); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeeeee eeeeee eeeeeeeee eeeeee ee eeeeeee eeee eeee eeeeeee eeee eee eeeeeeeee eeeeeeeee eeee eeeeeee ee ee 888°M ee eeee eeeeee eeee e eeeeee.

8-Meeeeeeeeeee eeee (88; 888eeee) eee eeeeeeeee ee MMMM. Meeee ee 8.88.8M eeee eeeeeeeee eeee eee eeeeeeeeeee eeeeeeeee eeeeeeeee. Mee eeeeeeeeeee ee 8-eeeeeeeeeeee eeee (88) ee MMMM eeeeeeee 888eee. Mee eeeeeee ee ee eeeeeeee (8eeee) eee eeee eeeee eeeeee ee e eeeee, eeeeee, ee eeeeeeeee ee MMMM (eee/ee MMM, ee eeeeeeeee). Mee eeeeeeee eee eeeeeeeee ee MMM. Meeeee eee eeeeeeeee ee eeeeeeee ee eee eeeeeee eeee M8M, eeeeeeeeee ee eee eeeee eeeeeeeeeee eee eeeeeeeeee ee eee eeeeeeee eeee ee eeeeeee eeeeeee. Mee eeeeeee eee eeee eeeeeeee eee eeeeeeee ee eeeeeeee eeeeeeeeee.

Meeeee-Meeeeeeeeee Meeeeee 88 ee MeeeMeeeee Meeeeeeeeee Meeeeeeee ee Meeeee-Meeeeeeeeee Meeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeee-eeeeeeeeeee eeeeeee (8.88eeee) eee eeeee ee e 8.88M eeee ee MeeeMeeeee ­eeeeeeeeeee (88) (8.88eeee) ee MM8Me8, eee eee eeeeeee eee eeeeeee ee ee eee 8e. Mee eeeeeee eee eeee eeeeeee eeee Me8M (88eM) eee eeeeee eeee e 8.88M eeee ee Me8M8M8 ee eee. ee MeMMM8. Mee eeeeee ee eee eeeeeeeeeee eeee eee eeeeeeeeee ee eeeee e eeeee-eeee eeeeee ee Me8M8M8 ee MeeeMeeeee eeeeeeeeeee (88) (eeeeeeeee 88eM). Mee eeeeee eeee eeee eeeeeeeee, eee eee eeeeeee eeeee eeeeee eeeeeeeeeeee eeee eee. ee MeMMM8 (8×88eM) eee M8M (8×88eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeee eeeeeeeee eeee Me8M (8×88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eee eee eeeeeee eeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee.

Meeeeeee (88) ee Meeeeeeee Meeee Meeeeeeeeee Meeeee ee ee Meeee Meeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeee ee eeeeeee (8eeee) ee 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee (8eM) eee eeeee MeeeMeeeee eeeeeeeeeee (88; 8.8eeee) ee ee eee eeeeeeee eee eeeeeeeee eee eee eeeeeeeeeee eeee. Meeee eeeeeeeeee ee eee eeeeeeee, ee eeeeeeeee ee MMM, eee eeeeeee eee eeeeeeeee eeee Me8M (8×88eM). Mee eeeeeeee Me8M eeeeeeee eeee eeeeeeeeeeee ee eeeee eee eee eeeeeeeee eeeeeee eee eeeeeeee eeeeeee eeee e eeeee eeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeeeee eee eeee eeeeeee; eeeee: 88%. Mee eeee ee eee eeeee eeeeee eee eeeeeee eeee M8M eee eeeeeeee ee eeeeee eeeeeeeeeee eeeeee. Mee eeeeeee eeeee eee eeeeeeeeeee ee eeeeeee eee eeeee eeeeee.

References