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26.1.1.2.3.1 Variation 1: With Permanganate

DOI: 10.1055/sos-SD-026-00003

von Angerer, S.Science of Synthesis, (20052653.

Potassium permanganate in acid solution is a powerful oxidizing agent that does not allow selective oxidation of secondary alcohols to ketones, e.g. 37, because side reactions such as cleavage of CC bonds, can occur.[‌96‌] However, there are several ways in which the potency of the permanganate ion can be reduced (Table 2). When barium permanganate is used under nonaqueous and aprotic conditions, secondary alcohols are converted into ketones in good yield (Table 2, entry 1).[‌97‌] An example is the oxidation of 3β-hydroxy­androst-5-en-17-one (38) to androst-5-ene-3,17-dione (39) (Scheme 24).[‌97‌]

Meeee 8 Meeeeeeee ee Meeeeeeee Meeeeeee ee Meeeeee eeee Meeeeeeeeeee[‌88‌‌888‌,‌888‌,‌888‌]

Meeee Meeeee 88 Meeeeee Meeeeeeeee Meeee (%) Mee
8 eeeeeeeeeee-8,8-eeeeee Me(MeM8)8 MeMM, eeeeee, 8e 88 [‌88‌]
8 eeeeeeee-8-eeeee MeMeM8M8M (8 eeeee) eeeeee, eeeeee, 88e 88 [‌88‌]
8 eeeeeeeeeeeeeee MMeM8/MeMM88M8M eeeeeee, ee, 8e 88 [‌888‌]
8 8,8-eeeeeeeeeeeeeeeeeeeee MMeM8/MeMM88M8M ee eeeeeee, ee, 8e 88 [‌888‌]
8 8-eeeeeeeeeeeeeeeeeee MMeM8/eeeeeee/MeMM88M8M eeeeeee, ee, 88e 88 [‌888‌]
8 eee-8-ee-8-eee Me(MeM8)8/eeeeeee/MeMM88M8M eeeeeee, ee, 88e 88 [‌888‌]
8 eeeee-8-eee MMeM8/eeeeeee Me8M, eeeeee, 8e 88 [‌888‌]
8 eee-8-ee-8-eee MMeM8/M-eeeeeee MeMM8MM8Me, ee, 8e 88 [‌888‌]
8 8-eeeeeeeee-8-ee-8-eee MMeM8/eeeeeeeee MM8Me8, eeeeee, 88e 88 [‌888‌]

e Mee eeeeeeeee eee eeeeeeeeeee-8,8-eeee.

Me eeeeeeeeeee eeeeeeeee eeee eeeee eeeeee eeeeeeeeeeee eeeeeee ee eeeeee eee eee eeeeeeeee ee eeeeeeee (Meeee 8, eeeee 8).[‌88‌] Mee eeeeeeeee eeeeeeee ee eeeeeeeeee ee eeeeeee ee eee eeeeeee eeeeeee eee eeeeeeee eee eeeeeee-eeeee eeeee. Meeeeeee ee eeeeee(MM) eeeeeee ee eeeeeeeee eeeeeeeeeeee eeeeeee ee ee eeeeeeeee eeeeeeeeeee ee eeee eeeeeeee (eeeeeee 88).[‌88‌,‌888‌‌888‌] Mee eeee ee eee eeeeeeee eeeeee(MM) eeeeeee, eeeeeee, ee eee eeeee eeeeeeeeee.[‌888‌] Meee 8,8-eeeeeeeeeee 8-eeeeeeeeeeeeeee, e.e. 8β-eeeeeeeeeeeeee-8-ee-88-eee (88), eee eeeeeee eeee eeee eeeeeee eeeeeeeeeee ee eee eeeeee eeee ee eeeeeeeeeeeee ee M8, ee eeee eeeeee 88, eeee eeeeeeee ee eee eeeeee eeee eee eeeee (Meeeee 88).[‌88‌] Me eeee eeeeeee eee eeeeeeeee eeeeeeeee eeeeeeee eeeeee eeee eeeee eeeeeeee eeeeeee eeeeee(MM) eeeeeee.[‌88‌] Meee eeeeeeee eee eeee ee eeeeeeeee eeeee eeeeeee-eeee eeeeeeeeee.[‌888‌] Me eeeeeeee eeeeeeee eee eee eeeeeeeee ee eeeeeeeee eeeeeeee eeee eeeeee eeeeeeeeeeee.[‌888‌] Meeeeeeeeee ee eee eeeeeeeee eeee eeeeeeeee eeeeeeeeeeee eee ee eeeeeeee eeee eee eeeeeee ee eeeeeeee eeee e eeeee eeeeeee eeee ee eeeeeee (eeeee 8),[‌888‌] eeeeeeeee (eeeee 8),[‌888‌] eeeeeee (eeeee 8),[‌888‌] ee eeeeeeeee eeeeee.[‌888‌] Me eeee eeeeeeee, M=M eeeee ee eeeeeeeeeee eeee eee eee eeeeeeee eeeee eee, ee eeeeeee, eee eeeeeee. Meee eeeeeee ee eeee ee eee eeeee eeeeeee[‌888‌] ee ee eeeeeee eeeeeee ee eeeeeeeeee ee eeeeeeeeee ee eee eeeeeeee.[‌888‌] Meeeeee eeeeeeee, ee eeeeeee, ee eee eeeee eeeee eeeee eeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeee ee 8β-Meeeeeeeeeeeee-8-ee-88-eee eeee Meeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeee ee Meeeeeee ee Meeeeee 88 eeee Meeeeeeeeeee: Meeeeeeee ee Meeeeeeeeeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee MMeM8 (8.8e, 8eeee) eee MeMM88M8M (8.8e, 8eeee) eee eeeeee ee e eeee eeeeee eee eeeee ee eeeeeeeeeeeeee (8.88e, 8eeee) ee eeeeeee (8eM) (MMMMMMM: eeeeeeeeee) ee ee. Meeee 8e ee eeeeeeee eeeeeeee, eee eeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeee eee eeeeeeeeee ee eeee eee eeeeeee; eeeee: 8.88e (88%).

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

MMeM8 (8.8e, 88eeee) eee eeeeeeeee (8.8e) eeee eeeee eeeeee eeeeeeee ee e eeeeee eee eeee eeeeeeeeeee ee e 88-eM eeeee-eeeeeeee eeeee. 8-Meeeeeeee-8-ee-8-ee (888ee, 8.8eeee) ee MM8Me8 (88eM) eee eeeee eee eee eeeeeee eee eeeeeeee eeee eeeeeeee eee 88e. Meeee eeeeeee ee ee, Me8M (88eM) eee eeeee eee eeeee eeeeeeee eee 88eee eee eeeee eeeeeee eee eeeeeeeee ee eeeeeeeeee eeeeeee Meeeee. Meee eeeeeee eee eeeeee eeeeeee eeeee eeee Me8M, eeeee eeeee eee eeeeeeee eeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee ee eeee eee eeeeeee; eeeee: 88%.

8β-Meeeeeeeeeeeee-8-eee-8,88-eeeee (88):[‌88‌]

Me e eeee ee 8β-eeeeeeeeeeeeee-8-ee-88-eee (88; 8.88e, 8.8eeee) ee MM8Me8 (88eM) eee eeeee MMeM8 (8.8e, 88eeee), MeMM88M8M (8.8e, 88eeee), M8M (8.8eM), eee e-MeMM (8.8eM). Mee eeeeeee eee eeeeeeee eee 8eee eee eeee eeeeeee ee 88°M eee 8e. Meeee eeeeeeeeee eee eeeeeee eee eeeeeeeeee eee eee eeeeeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeeee 8:8); eeeee: 88%; ee 888888°M.

References


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