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Please login to access the full content or check if you have access via Variation 7: With Organic Iodine(III) Compounds

DOI: 10.1055/sos-SD-026-00003

von Angerer, S.Science of Synthesis, (20052671.

In comparison to iodine(V) reagents such as 2-iodylbenzoic acid (75) and DessMartin per­iodinane (76) the reactivity of iodine(III) reagents toward alcohols is normally low and ­catalysts have to be employed in these reactions. Two reagents have proved appropriate for the oxidation of secondary alcohols: phenyliodine diacetate (81, R1=H)[‌222‌,‌223‌] and iodosylbenzene (82; phenyliodane oxide),[‌224‌‌226‌] which is readily prepared from the alkaline hydrolysis of phenyliodine diacetate (Scheme 54).

Meeeee 88 Meeeeeeee ee eee Meeeee(MMM) Meeeeeee, Meeeeeeeeeee Meeeeeeee eee Meeeeeeeeeeeee eeeee eeee e Meeeeeee(MMM)Meeee Meeeeeee[888-888]

Me eee eeeeeeee ee e eeeeeeeee eeeeee (88%) ee 8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee, eeee­eeeeeeeeee (88) eeeeeeee eeeeeeee eeeeeeeeeee ee eeeeeeee eeeeeeeee eeee eeeeeeeeee eee eeeeeee eeeeeee eeeeee.[‌888‌] Meeee eeeeeeeee, eeee ee eee eeeeeeee(MMM)eeeee eeeeeeee 88, eee eeee ee eeee ee eeeeeeeeeee eeee eee eeeeee(MMM) eeeeeeee. Meeeeeeeeeeeee eeeeeeee eee eee eeeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeee 88 eeee eeeeee(MMM) eeeeeeee eee eeeee ee Meeee 8.

Meeee 8 Meeeeeeeee eeee Meeeee(MMM) Meeeeeeee[888-888]

Meeee Meeeee 88 Meeeeee Meeeeeee Meeeeeeeee Meeee (%) Mee
8 8-eeeeeeeeeeeeeeeeeeee 88 (M8=M) MMMMM MM8Me8, ee, 8e 88 [‌888‌]
8 (8M)-eeee-8-ee-8-eee 88 88 MMMMe, MM8Me8, ee, 8e 88 [‌888‌]
8 eeeeeeeeeeeee 88 (M8=MM8) MM8MMe8 88°M, 8.8e 88 [‌888‌]
8 8-eeeeeeeeeeeeeee-8-eee 88 Me(MM8)8 8,8-eeeeeeeeeeeeee, 88°M, 8.8e 88 [‌888‌]
8 8-eeeeeeeeeeeeeee-8-eee 88 MMe M8M, ee, 8e 888 [‌888‌]

e 8-Meeeeeeeeeeeee M-eeeee.

Me eeeeeeeee eeeeeeee eee eee eeeeeeeee ee α,β-eeeeeeeeeee eeeeeeeee eeeeeeee eeee eeeeeeeeeeee eeeeeeeee (88) ee eeeeeeeeeeeeee (88) ee eee eeeeeeee(MMM)eeeee eeeeeee, [eee(eeeeeeeeeeee)eeeeeeeeeeeeeee]eeeeeeee(MMM) eeeeeeee (88) (Meeee 8, eeeee 8).[‌888‌,‌888‌,‌888‌] Meee eee eeeeeeee eeeeeeeeee ee eeeeeeee eeee eeeeeeeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeee ee α-eeeeeee eeeeeeee eee eeeeeeee eeeee eeee eee eeeeee.[‌888‌] M eeeee eeeeee ee eeeeee eeee eeee eeee 8% eeeeeee ee eeeeeeeeeee eeee eeee eeeeeeee eeee eee eeeeee­ee(MMM)eeeee eeeeeeee eeeeeee ee eee eeeeeeee ee eee eeeeeeee 8-eeeeeeeeeeeeee M-eeeee. Mee eeeeeeee eeeeeeee(MMM)eeeee eeeeeee, eeeee ee eeeeeeeeee ee ee eeeeeeee ee e eeeeeeee(M) eeeeeeeeeeee, eee eeee eeeeeeee ee eeeeeeeeeeee ee eee eeeeeeee eeeee eee eeee ee eeeee eeeeeeeee ee eeee eeeeee.[‌888‌]

Meeee eeeeeeeeeeeeeeeeee eeeee eeeeeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeee eeee 8-eeeeeeeeeeeeeeeee eeeeeeeee (88; M8=MM8) ee eeeeeeeeeee ee eee eeeeeeeeee ee eeeeeeeeeeee eeee eeeeeeeeeeeee (Meeee 8, eeeee 8). Meeeeeeeeeeeee (88) eeeeeeee e eeeeeee ee eeeeeeee ee eeeee eeeeeeeeeeeee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee eeee ee eeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM), eeeeeee eee eeeeee eee eee eeeeee eeeeeeeeeeee eee eeeeeeeee eeeeeeee eeee eeee eeeee ee eeeeeeeee.[‌888‌] Me eeeeeeeeeee eeeeeeee eee eee eeeeeeeee eeee eeeeeeeeeeeeee (88) ee eeeeeeeee(MMM) eeeeeee (Meeee 8, eeeee 8).[‌888‌] Meeeeeeeeeeeee (88) eee eeee ee eeee ee eeeeeee eeeeeeee eeeeeeee eeee (8-eeee­eeeeeeeeeee)eee eeeeeee eeee eee eeeeeeeee ee eeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeee ee 8-eeeeeeeeeeeeeee eeee.[‌888‌]

Mee eeeeeeeee ee eeeeeeeee eeeeeeee eeee eeeeeeeeeee eeeeee(MMM) eeeeeeee ee eeeeeee eee ee eeeeeee eeeeeeeee eeee eeeeeeeeeeeeee (88) ee eeeee eeee 8 eeeeeeeeee ee eeeeeeeee eeeeeee ee eeeee (Meeee 8, eeeee 8).[‌888‌,‌888‌] Meeee eeee eeeee eee eeeeeee eee eeeeeeeeeeeee, eee eeeeeeee ee eeeeeeeeee ee eeeeeee eee eee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeee (88) ee eeeeeeee ee eeeeeee ee eee eeeeee eeee, eeeee eeeeeeeeeee eee eeeeee ee eee eeeeee(MMM) ee eee eeeeee ee eee eeeeeee.

Meee eeeeeeeee eee ee eeeeeeee ee eeeee e eeeeeee-eeeeeeeee eeeeee(MMM) eeeeeee, eeeee ee eeeeee eeeeeeee ee eeeeeeeeee ee eeeeeeeeeee eee eeeeeeeeee eeee eee eeeeeeeeeeee eeeeeeeee eeeeeeeeee 88 (Meeeee 88).[‌8‌] Mee eee eeeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeee eee eeee eeeeeeeee, 8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee eee eeeeeeeee eeeeeee, eeee eee eee eeeeeeeee eeeeeeee eee ee eeeeeee.[‌888‌,‌888‌] Me eeeeeee ee eee eeeeeeeeeee ee eeee eeeee-eeeeeeeee eeeeee(MMM) eeeeeee ee eee eeeeeeeeee ee eeeeeeeeee eeee eeeeeee (88) (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeee ee e Meeeeee-Meeeeeeee Meeeee(MMM) Meeeeee eee Mee Meeeeeeeeee ee eee Meeeeeeee ee Meeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee 88 ee Meeeeeeee eeee Meeeeeeeeeee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee eee eeeeeee (8eeee) eee MMMMM (88ee, 8.8eeee) ee MM8Me8 (8eM) eee eeeee 88 (888ee, 8.8eeee). Mee eeeeeee eee eeeeeee eeeee eee eeeeeee eee ee eeeeee eeeeeeeeee (MMM), eee eeeeeee eeee MM8Me8 (8eM). Mee eeeeeee eee eeeeee eeee eee. ee Me8M8M8 (8eM) eee eeeeeeeee eeee MM8Me8 (8×8eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee ee MeMMM8 (8eM) eee eeeee (8eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeee eeeeeeeeeeeeee ee eeeeeeeeeeeeeee eeeeeeee eeee eeeeeeee ee 8888% eeeee.

Meeeeee 88 ee Meeeeeeee eeee Meeeeeeeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

M8M (8.8eeee) eee eeeee eeeeeeee ee e eeeeeee eeeeeee ee eee eeeeeee (8.8eeee), eeeeeeeeeeeeee (88) (88.8ee, 8.88eeee), eee MMe (88.8ee, 8.8eeee). Mee eeeeeee eee eeeeeee ee eeeeeeeee eee eeeeeee e eeeee eeeeeeee eee eeeeeeee eeeeeeee ee MM ee MMM. Meeee eeeeeeeeee, eeeeee eee eeeee eee eee eeeeeee eee eeeee (Me8MM8) eee eeeeeeee. Meeeeeeeeee ee eee eeeeeee eeeee eeeeee eeeeeeee e eeeee eeeeeee eeee eee eeeeeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (Me8M/eeeeee) ee eeee eee eeee eeeeee ee eeeeeeeee eeeeeeeeeeee eeeee.

Meeeeeeee ee Meeeeee (88) Meeee e Meeeeee-Meeeeeeee Meeeee(MMM) Meeeeee; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eeeeeeeeeee (MM ee. 888 888; 88e, 888eeee), M8 (88e, 88eeee), M8M8 (8e, 88eeee), MMe8 (88eM) (MMMMMMM: eeeee), eee 88% M8MM8 (88eM) ee eeeeeeeeeeee (888eM) eee eeee ee 88°M eee 88e. Mee eeeeeee eee eeee eeeeeee eeee MMMe8 (888eM) eee eeeeeeeeeeee ee eee eeeeeeee ee MeMM (8888eM). Mee eeeeeeeeeeee eeee eeeeeeeee ee eeeeeeeeee ee eeee eeee(8-eeeeeeeeeee); eeeeeee eeee ee eeeeeeeeee eeeeee 8.8eeee·e8. 88% M8M8 (88eM) eee eeeee eeeeeeee ee Me8M (888eM) ee 8°M. Mee eeee eee eeeeee eeeeee ee ee, eee eeeeeee eeeeeeeee. Me eeee eeee eee eeeee eeee(8-eeeeeeeeeee) (8e) eee eee eeee eee eeee ee 88°M eeeeeeeee. Meeee eeeeeee, Me8M eee eeeee ee eee eeee ee eeeeeeee­eee eeee[8-(eeeeeeeeeeeee)eeeeeee] 88 (ee. 8e), eeeee eee eeeeeeeee ee eeeeeeeeee; eeeeeee eeee ee (eeeeeeeeeeeee)eeeeee eeeee 8.88.8eeee·e8.

Me e eeee ee eeeeeeeeee (8eeee) eee MMMMM (88ee, 8.8eeee) ee eeeeeee (8eM) eee eeeee 88 (888ee, 8.8eeee), eee eee eeeeeee eee eeeeeee ee ee eee 8888e. Me eee eee ee eeeeeeee, Me8M (88eM) eee eeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eee eeeeeee. Meeee eeeeeee ee eee eeeeeee eeee eee eeeeeeee, eee eeeeeeeeeeeee eeeeee eee eeeeeeee ee >88% eeeeee. Me eeeeeeeee, eee eeeeeeee eee eeeeee eeee M8M eee eeeeeeeee eeee Me8M (8×88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eee eeeeeee eeeeeee ee eeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee) ee eeee eee eeee eeeeeee; eeeee: 88%. Mee eeeeeee eee ee eeeeeeeeeee ee eeeeeeee ee eeee eeeeeeeee eeee.