The Bayer-Villiger Oxidation of Aldehydes and KetonesC. H. HassallOrganic Reactions, Vol. 9, Ch. 3, pp. 73-106 (1957)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/bayer-villiger.or-a.pdf)
ContentsIntroductionMechanism of the ReactionScope of the Reaction Saturated Aliphatic Ketones Alicyclic Ketones
Aromatic Ketones
,
-Unsaturated Ketones
Polycarbonyl Compounds
Aldehydes
Side Reactions
Selection of Experimental ConditionsPeroxides
Hydrogen Peroxide
Persulfuric Acid
Perbenzoic Acid
Monoperphthalic Acid
Peracetic Acid
Solvents and Catalysts
Temperature and Time
Experimental ProceduresCatechol
3,4-Dihydroxyphenanthrene
Phenyl p-Nitrobenzoate
Etiocholan-3
,12
,17
-triol
Diphenic Acid
2-Acetoxyindan-1,3-dione
Lactone C
21H
32O
4 from Isoandrosterone Acetate
Tabular Survey of the Baeyer-Villiger Reaction Table I. Oxidation of Saturated Aliphatic Ketones
Table II. Oxidation of Alicyclic Ketones
Table III. Oxidation of Aliphatic, Aromatic, Alicyclic Aromatic, Aromatic, and Heterocyclic Ketones
Table IV. Oxidation of
,
-Unsaturated Carbonyl Compounds
Table V. Oxidation of Polycarbonyl Compounds
Table VI. Oxidation of Aldehydes
This review should come in handy for the procedures discussed in the following threads:
Post 432975
(Aurelius: "Baeyer-Villiger Oxid. --> Methoxybenzaldehydes", Methods Discourse)Post 472943
(bio: "Benzaldehyde + MEK acid catalyzed aldol", Methods Discourse)Post 477679
(Rhodium: "Syntheses of Dillapiole & its 4-Methylthio analog", Chemistry Discourse)Post 446838
(GC_MS: "SPC/SPB", Novel Discourse)Post 397551
(demorol: "Phenols from aldehydes", Novel Discourse)