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Please login to access the full content or check if you have access via 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]

Meeeee 8 Mee Meeeeee MeeeeeMeeeeeee Meeeeeeee[‌8‌‌88‌]

Meeee eee eee eee eeeeeeee eeee eeee eee eeeeeeee ee eeeee eeeee. Meeeeee, eee eeeeeeeeeeeeee ee eeeeeeeee ee eeeeeeeeeee, eee ee eeeeeee ee eee eeeee: eeeeeeee > eeeeeeeee > eeeee eee eeeeeee > eeeeeeeeeee > eeeeee.[‌8‌,‌88‌,‌88‌] Meee eeeee ee eeeeeee eeeeeeeeee ee eee eeeeeeeee eeeeeee ee eeeeeee eeeeee ee eeee e eeeeeee eeeeeeee eeeeee eeee eeee eeeeeee. Mee eeeeeee e β-eeeee eeeeeeeeeee eeeeeee eeeeeeeee (eee Meeee 8, eeeee 88), ee ee eeeeee eeeeee eee eeeeee (Meeee 8, eeeee 88). Meeeeeee-eeeeeeeeeee eeeeee eeeeee eee eeee ee eeeeeeee. Me eeeeee eeeee eee eeee ee eeeeeeeeeeeeeeee eeeeeee eee eeee eeeeee eeeeeeee.[‌88‌] Meeeeeee, eee eeeeeeeee eeeeee eeee eeeeeeeee ee eeeeeeeeeeeeeee ee eee eeeeeeeee eeeeee.[‌88‌,‌88‌]

Mee eeeeeeeee ee eee eeeeeeee eee eeee eeeeeee ee eeeeeeeeeee eeeeee eee eee eeeeeeee eeeeee eeeeee eeeeeeee ee eeeee ee Meeeee 8. Meeeee eeee eeeeeeeee eeeeeee eeeeeeeeeee ee eeeeeee eee eee eeeeeeeee ee eeeeeee eeee ee eeeeeeee eeeeee eee eeeeeeee.[‌88‌] Mee eeee ee MeeeeeMeeeeeee eeeeeeeee eeeeeeee ee eeeee eeeeeeeee ee eeeeeeeee eeeeeeeee, eee eeeee eeeeeee eeeeeeeeee eeeeeeeeeee ee eeeeeeee.

Meeeee 8 MeeeeeMeeeeeee Meeeeeeee[‌88‌]

Meee eeeee, eee eeeeeeee ee eeeeeeeee ee eeeeeeee e eeeeeeee ee eee eeeeee ee eeeeeeeeeeeeeee ee eeeeeeeeee eeee e eeeeee eeee eeee ee 8-eeeeeeeeeeeeeeeeeee eeee ee eeeeeeeeeeee eeeeeee 8 eee 88°M (Meeee 8, eeeeeee 8, 8, 8, 8888). Meeee eeeeeeee eeeeeeee eeeeee eeeee eeeeeee eeeeeeeee eeee, eeeeeeeeeeeeeeeeee eeee (Meeee 8, eeeeeee 8 eee 8) (eeeeeee eeeeeeee eeeeeeeeeee eeeee ee eee eeee eeeeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee eeee eee 88% eeeeeeee eeeeeeee[‌88‌] ee eeeeeeeeeeee eeeeeeee eeeeeee[‌88‌]), eeeeeeeeeeeeeeee eeee, eeeeeeeeeeeeeeeeee eeee, eeeeeeeeeeeee eeee, 8-eeeeeeeeeeeeeeeeee eeee, eee 8,8-eeeeeeeeeeeeeeeeeeee eeee (Meeee 8, eeeee 8). Meeeeeee eeeeeeee ee eeee eeeeeeee, eeeeeeeeeeee eee eeeeeee eeee eee eeeeeee eeeeeeeee eeee eeeeee eeeeeeeeeee. M eeeeeee ee eeee eeeeee eeeeeeee eeee eeee eeee eeee, eeeeeeeee eeeeeeeeeeeeeeeeeeeeee eeee (Meeee 8, eeeee 8), eeeeeeeee eeee, eeeeeeeee, eee eeeeeeeeeeeee(MMM) eeeeeeeeeeeee eeeeeeee.[‌88‌] Meeeeeeee eeeeeee,[‌88‌] eeeeeeeeee eeeeeeee,[‌88‌] eee eee eee ee eeeee eeeeeee[‌88‌] ee eeeeeeee eee eeee eeeee.

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 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,
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%).