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25.6.1.1.3 Variation 3: Cleavage by Permanganate and Periodate

DOI: 10.1055/sos-SD-025-00380

Ditrich, K.Science of Synthesis, (200725526.

Although a strong oxidant in aqueous acidic or basic conditions, the chemical properties of potassium permanganate are remarkably changed by using solid supports. Whereas alkenes, e.g. 8, are normally cleaved by aqueous permanganate to the corresponding carboxylic acids, oxidation with solid-supported permanganate reagents leads to the formation of aldehydes 9 (Scheme 4).[‌14‌] From a wide variety of supports, alumina and Amberlite IR-120 are the most effective. The experimental procedure is operationally simple: the immobilized permanganate is reacted with the substrate in an organic solvent; upon completion of the reaction, excess reagent and byproducts are removed by filtration and nearly pure products are obtained by removal of the solvent.

Meeeee 8 Meeeeeee ee Meeee-Meeeeeeeeee Meeeeee ee Meeeeeeeeeee[‌88‌]

Meeeeeeee eeeeeeeeee eeeeee eee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeee eee e eee-eeee eeeeeeee eeeeeeee eeeeeeeeee ee (8) eeeeeeeeeeee ee eee eeeeeeeee eeeeeeeeee eeeeeeee 88 eeee eeeeeeeeeeeeeeeee eeeeeeee eeeeee (88) ee eeee ee eeeeeee 88 eee (8) eeeeeeeee eeeeeeee ee eee eeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeee 88 (Meeeee 8).[‌88‌] Meeee eeeeeeeee eeeeeeeee ee eee eeeeeeeee eeeeeee M=M eeee eeeee eeeeeee eeeeeeeee ee eeeeee ee eeeeeeeee eeeeeeeee (eee Meeeeee 88.8.8.8.8); eeeeeeeeeeeeeeeeeeeee eee eeee eeeeeeeeee ee eeee eeeeee ee 8888% eeeee.[‌88‌]

Meeeee 8 Meeeeeeee-Meeeeeee Meeeeeee ee Meeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeeeee (8, M8=MMe; M8=M); Meeeeee Meeeeeeee:[‌88‌]

MMeM8 (8.88e, 8.8eeee), M8M (8.88e), eee eeeeeee (8.88e; eeeeee, eeeeeeee 8) eeee eeeeeeee ee e eeeeee eee eeeeee eeeee e eeeeeeeeeee eeee eeeeeeee. Me e eeee ee (M)-8-(8-eeeeeeeeeeeee)eeee-8-eee (8, M8=Me; M8=MMe; M8=M; 8.888e, 8eeee) ee MM8Me8 (88eM) eee eeeee eee MMeM8/eeeeeee eeeeeee (8.88e). Mee eeeeeeeeeeeee eeeeeee eee eeeeeee ee ee eeeee MMM eeeeeeee eeeeeeeee eeee eee eeeeeeee eee eeeeeeee (8e). Mee eeeeeee eee eeeeeeee eeeeeee Meeeee eee eeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee; eeeee: 8.888e (88%); 8MMMM (MMMe8, 888MMe, δ): 8.88 (e, 8M), 8.88 (e, 8M, M=8.8Me), 8.88 (e, 8M, M=8.8Me), 8.88 (e, 8M).

Meeeee 8-[8-(Meeeeeeeeeeee)eeeee]-8-eeeeeeeeeeeee (88, M8=MM8; M8=MM8Me; M8=M); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeee 8-eeeeee-8-eeeeeeeeeeeee (88, M8=MM8; M8=MM8Me; M8=M; 888.8e, 8.8eee) eee eeeeeeeee ee eee MMM (8M). Meee eeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeee eeeeee (88; 888.8e, 8.8eee) eee eeeeeee eee eeeeee ee 888°M; eeeeeee eeeeeeeee eee eeeeeeee eeeeee 8e. Mee eeeeeeee eeeeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeeee eee eeeeeeeeeeeeee (MeMM) ee eeee eee eeeeeee; eeeee: 888.8e (88%); ee 8888°M.

Meeeee 8-Meeeee-8-eeeeeeeeeeeee (88, M8=MM8; M8=MM8Me; M8=M):[‌88‌]

M eeeeeee ee eeeeeee 88 (M8=MM8; M8=MM8Me; M8=M; 88.8e, 888eeee) eee MeMM8 (888.8e, 888eeee) ee 88% ee MMM (8M) eee eeeeeee ee ee eeeee MMM eeeeeeee eeeeeeeee eeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeeee (ee. 8e). Meeeeeeee eeeee (MeMM8) eeee eeeeeee ee eeeeeeeeee eee eeeeee eeee MeMMe (8×888eM). Mee eeeeeeee eeeeeeeee eeee eeeee (MeMM8) eee eee eeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeee 8:8); eeeee: 88.8e (88%); ee 8888°M.

References


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