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20.5.1.6.1 Method 1: Baeyer–Villiger Oxidation

DOI: 10.1055/sos-SD-020-00757

Phillips, A. J.; Love, C. E.Science of Synthesis, (200720827.

The conversion of ketones (and aldehydes) into esters by reaction with peroxy species such as 3-chloroperoxybenzoic acid, hydrogen peroxide, or tert-butyl hydroperoxide is known as the BaeyerVilliger oxidation (Scheme 1). The reaction is of substantial importance to synthesis and has been reviewed a number of times. The reader is directed to these reviews for specific information outside the context of this brief survey.[‌1‌‌10‌]

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Meeeee 8 MeeeeeMeeeeeee Meeeeeeee[‌88‌]

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M eeeeeeeee ee eeeeeeeeeeeeee eeeeeeee ee MeeeeeMeeeeeee eeeeeeeee eee eeeee ee Meeeee 8 eee Meeee 8. Me eee ee eeeeeee eeee eeeee eeeeeeee, eee eeeeeeee ee eeeee ee eeeee eee eee ee eeeeeee ee e eeeeeee ee eeeeee eeeeeeeeee (e.e., eeeeeee 8, 8, 8, eee 8; eee eeee Meeeeee 88.8.8.88) eee eeeeeee eeeeeeeeee, ee eeee eee eeeeeeeeeeeee eeeeee, e.e. 8, 8, 8, eee 8.

Meeeee 8 MeeeeeMeeeeeee Meeeeeeeeeeeee[‌88‌‌88‌]

Meeee 8 Meeeeeee MeeeeeMeeeeeee Meeeeeeeeeeeee[‌88‌‌88‌]

Meeee Meeeeeee Meeeeeeeee Meeeeee Meeee (%) Mee
8 MMMM (8 eeeee),e MM8Me8,
88°M, 88e
88 [‌88‌]
8 88% M8M8, MeMeM8M, Me8MMM8,
MMM eeee eeeeeeeeeeeeee
88 [‌88‌]
8 MM8MM8M, MM8Me8, eeeeee, 88e 88 [‌88‌]
8 88% MM8MM8M, Me8MMM8,
MM8Me8, 88°M
88 [‌88‌]
8 MMMMM, MM8Me8, 88°M 88 [‌88‌]
8 8. MMMMM, MM8Me8, 88°M
8. M8MM8, MeMM/M8M (8:8)
88 [‌88‌]
8 MMMMM, MeMM (eee.), MM8Me8 88 [‌88‌]
8 MMMMM, MeMMM8, MM8Me8 88 [‌88‌,‌88‌]
8 88% M8M8, MeMM 88 [‌88‌]
88 MMMMM, MeMMM8, MM8Me8,
888°M
88 [‌88‌]
88 MMMMM, MM8Me8 88 [‌88‌]
88e MMMMM, MM8Me8, ee, 88e 888 [‌88‌]
88 MMMMM, MeMMe, 88°M >88 [‌88‌]

e MMMM = 8,8-eeeeeeeeeeeeeeeeeeee eeee.

e MMM=8,8-eeeeeeeeeeeeee.

Mee eeeeeeeee ee eeeeeee ee eee eeeeeeee ee eeeeeee ee eeeeee eeeeeeeee eeeeeeeee, eee eeee eee eeeeeeeeeee eee MeeeeeMeeeeeee eeeeeeee eeeee eeeee ee eeeeeeeeee eeeee.[‌88‌] Mee eeeeeeee ee eeee eee eeeee eee MeeeeeMeeeeeee eeeeeeee, eee e eeeeeeee(MMM) eeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeee eeee eeeeeeeee eeeeeee eee eeee eeeeeeee (Meeeee 8).[‌88‌] Me ee eeee eeeeeeee ee eeeeeee MeeeeeMeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeee eeee eee(eeeeeeeeeeeeee) eeeeeeee eee eee(MM) eeeeeeee.[‌88‌,‌88‌] MeeeeeMeeeeeee eeeeeeeee ee eeeeeeee eeeeeeee eeeeeee eeeeeeeeee eeeeeee eeee eeeeeeee eeeeeeee eeeee eeeee eeeeeeeeee ee eeee eeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

(8eM*,8eM*,8eM*,8eM*)-8,8,8e-Meeeeeeeeeeeeeeeeeeeeeeeeee[e]eeeeeeeeee[e]eeeee-8(8M)-eee (8); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeee 8 (888ee, 8.88eeee), Me8MMM8 (888ee, 8.88eeee), eee eeeee MM8MM8M [eeeeeeee eeee (MM8)8MMM8M8 (8e) eeeeee eee MMMM (8eM) ee eee MM8Me8 (8eM) ee 88°M] ee eee MM8Me8 (8eM) eee eeeeeee ee 88°M eee 8e. Mee eeeeeee eee eeeeee eeee eeeee (8eM), eeeee, eee eee eeeeeee eee eeeeeeeeee. MMM eeeeeeee ee eee eeeee eeeeeee eeeeee eee eeeeeeee ee e 8:8 eeeeeee ee eeeeeeee, eeeeeeeeee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee. Mee eeeeeee ee eeeeeeee eee eeeeeee ee e eeeeee (eeeeee eee, MeMMe/eeeeee 8:88) eee eeeeeeeee 8 ee e eeeeeee eeeeee; eeeee: 888ee (88%); eee eeeeeeee eeeeeee eee eeee eeeeeeee; eeeee: 88ee (88%).

Meeeee (8eM*,8M*,8eM*)-8-(8-Meeeeeeeeeee)-8-eeeeeeeeeeee-8M-eeee[8,8-e]eeeeeee-8-eeeeeeeeeee (8); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeeeeee ee eeeeeeeeeeeee 8 (8.88e, 8.8eeee) eee MeMMM8 (8.88e, 8.8eeee) ee MM8Me8 (88eM) ee ee eee eeeee MMMMM eeeeeeeeeee. Meeee eeeeeeee ee eee MMMMM, eee eeeeeeeeee eee eeee eeeeeeee eee ee eeeeeeeeee 88eee, eeee MMM eeeeeeeee eeeeeeee eeeeeeeeeee ee eee eeeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeeeeee ee e eeeeeeeeee eeeeee eee eeeeee eeee eee. Me8MM8 eeee (8 × 88eM) eee eee. MeMMM8 eeee. Mee eeeeeee eeeee eee eeeeeeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeeeee eee. Meeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8.8) eeee eee eeeeeee; eeeee: 8.88e (88%).

(8M,8M)-8,8-Meeeeeeeeeeeee-8-eee (8); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee 88% MMMMM (8.88e, 88.8eeee) ee MM8Me8 (88eM) eee eeeee eeeeeeee ee ee ee (M,M)-8 (8.88e, 8.8eeee) ee MM8Me8 (88eM). Mee eeeeeee eee eeeeeee eee 88e, eee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee, eee eee eeeeeeee eee eeeeee eeee eee. MeMMM8 eeee (8 ×) eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeeeee/Me8M 8:8) ee eeee eee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 888ee (88%).

8-Meeeeeeeeeeeeeeeeeee-8-eee (8):[‌88‌]

Me e eeeeeee ee eee eeeeee 8 (888ee, 8eeee) eee Me(MMe)8 (88ee, 8.8eeee) ee eeeee MM8Me8 (88eM) ee 8°M eee eeeee eeeeeeeeee eeeee (88% eeeeeeee) MMMMM (888ee, 8eeee), eee eee eeeeeee eee eeeeeee ee ee eee 8e. Meeee eeeeeeeeee ee eee eeeeeeee, eeeeee MMMMM eee eeeeeeeeee ee eee eeeeeeee ee ee Me8M8M8. Meeeeeeeeeee eeeeeee eeeeee, eeeeeeee ee eeeeeeeeeeee (eeeeee eee), eeee eeeeeee 8; eeeee: 888ee (88%).

References