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BAEYER-VILLIGER-reaction

In 1899, the Germans, A. Baeyer and V. Villiger, found that treating a ketone with a peroxy-acid (RCO3H) can produce an ester. An oxygen atom is inserted next to the carbonyl group. [Pg.992]

you saw a similar insertion5 reaction earlier in the chapter, and the mechanism here is not dissimilar. Both peracids and diazomethane contain a nucleophilic centre that carries a good leaving group, and addition of peracid to the carbonyl group gives a structure that should remind you of a semipinacol intermediate with one of the carbon atoms replaced by oxygen. [Pg.992]

Baeyer-Villiger reactions are among the most useful of all rearrangement reactions, and the most common reagent is m-CPBA (meta-chloroperbenzoic acid) because it is commercially available. [Pg.993]

Unsaturated ketones may epoxidize or undergo Baeyer-Villiger rearrangement [Pg.994]

Peracids may epoxidize alkenes faster than they take part in Baeyer-Villiger reactions, so unsaturated ketones are not often good substrates for Baeyer-Villiger reactions. The balance is rather delicate. The two factors that matter are how electrophilic is the ketone and how nucleophilic is the alkene You might like to consider why this reaction does work, and why the C=C double bond here is particularly unreactive. [Pg.994]

The Baeyer-Villiger reaction has solved a regioselectivity problem here. L-tyrosine, a relatively cheap amino acid, can be converted to the important drug L-dopa provided it can be hydroxylated ortho to the OH group. This is where electrophilic substitutions of the phenol take place, but electrophilic substitutions with HO are not possible. However, after a Friedel-Crafts acylation, the acyl group can be converted to hydroxyl by the Baeyer-Villiger reaction and hydrolysis. The Baeyer-ViUiger reaction means that MeCO can be used as a synthetic equivalent for Note [Pg.994]


Obsolete uses of urea peroxohydrate, as a convenient source of aqueous hydrogen peroxide, include the chemical deburring of metals, as a topical disinfectant and mouth wash, and as a hairdresser s bleach. In the 1990s the compound has been studied as a laboratory oxidant in organic chemistry (99,100). It effects epoxidation, the Baeyer-Villiger reaction, oxidation of aromatic amines to nitro compounds, and the conversion of sodium and nitrogen compounds to S—O and N—O compounds. [Pg.97]

Quantum, by contrast, converted an ethylene—carbon monoxide polymer into a polyester-containing terpolymer by treatment with acidic hydrogen peroxide, the Baeyer-Villiger reaction (eq. 11). Depending on the degree of conversion to polyester, the polymer is totally or partially degraded by a biological mechanism. [Pg.476]

A variety of esters can be prepared from the corresponding ketones usiag peracids ia a process usually referred to as the Baeyer-Villiger reaction (95) ie, cyclopentanone is converted to 5-valerolactone upon treatment of the ketone with peroxytrifluoroacetic acid ... [Pg.382]

The final step is not a radical reaction, but an example of the Baeyer-Villiger reaction, which will be discussed in Section 12.5.2 of Part B. [Pg.708]

While the oxidation of ketones by peracids (Baeyer-Villiger reaction) has been used in steroids mainly for ring cleavage, it has occasionally been applied to 20-ketopregnanes for conversion to 17-acetoxy- or hydroxyandros-tanes. The synthetic utility of this method is limited since reactive double bonds and other ketones are incompatible with the reagent. [Pg.151]

More recently, permaleic acid has been recommended as a very satisfactory reagent for the Baeyer-Villiger reaction. It reacts almost as fast as trifluoroperoxyacetic acid and does not require buffering. Unfortunately, neither of these two reagents has been used extensively on 20-keto steroids a patent claims the conversion of progesterone to testosterone acetate with trifluoroperoxyacetic acid, but a later communication describes the ready reaction of 3-keto-A" -steroids with this reagent. [Pg.153]

In the one application reported for the conversion of the 17jff-acetyl side-chain to the 17-ketone, the intermediate oxime was not isolated, but hydrolyzed in situ with acid in an overall yield of about 20 %. In the case of 17jff-acetyl-D-norandrostanes, which are particularly difficult to degrade to D-norandrostanes, the nitrite procedure proved the most convenient method. The yield is 25 %, nowhere near the much higher yield obtained by a Baeyer-Villiger reaction which, however, must be allowed to proceed for one month at 0°. ... [Pg.154]

Modern variants are the enzyme-catalyzed and the transition-metal-catalyzed Baeyer-Villiger reaction, allowing for an oxidation under mild conditions in good yields, with one stereoisomer being formed predominantly in the enzymatic reaction ... [Pg.21]

The Dakin reaction proceeds by a mechanism analogous to that of the Baeyer-Villiger reaction. An aromatic aldehyde or ketone that is activated by a hydroxy group in the ortho or para position, e.g. salicylic aldehyde 12 (2-hydroxybenzaldehyde), reacts with hydroperoxides or alkaline hydrogen peroxide. Upon hydrolysis of the rearrangement product 13 a dihydroxybenzene, e.g. catechol 14, is obtained ... [Pg.21]

The epoxidation reaction usually takes place under mild conditions and with good to very good yield. Functional groups that are sensitive to oxidation should not be present in the starting material with carbonyl groups a Baeyer-Villiger reaction may take place. [Pg.232]

The original library of 10 000 clones used in the Baeyer-Villiger reaction [89] was screened for performance as potential catalysts in the sulfoxidation [32]. This led to the discovery of at least 20 mutants having enantiomeric excess values in the range of 85-99%, some being (R) selective and others being (S) selective. Five mutants resulting in enantiomeric excess values of >95% were sequenced (Table 2.2) [32]. [Pg.53]

In another kind of reaction, an aromatic aldehyde ArCHO or ketone ArCOR is converted to a phenol ArOH on treatment with alkaline H202, but there must be an OH or NH2 group in the ortho or para position. This is called the Dakin reac-The mechanism may be similar to that of the Baeyer-Villiger reaction (18-19) ... [Pg.1528]

Another approach is to use the Baeyer-Villiger reaction we have Just carried out to make (34), esterify. and oxidise to the ketone. [Pg.325]

Hydroxylation and Baeyer-Villiger reactions carried out by monooxygenation are important in the degradation of a range of terpenoids and steroids. The aerobic degradation of limonene can take place by a number of reactions several of which involve hydroxylation at allylic positions... [Pg.339]

The Baeyer-Villiger reaction has found considerable application in the synthesis of prostaglandins. One common pattern involves the use of bicyclo[2.2.1]heptan-2-one derivatives, which are generally obtained by Diels-Alder reactions. For example, compound 10 is known as the Corey lactone and has played a prominent role in the synthesis of prostaglandins.237 This compound was originally prepared by a Baeyer-Villiger oxidation of 7-(methoxymethyl)bicyclo[2.2.1]hept-5-en-2-one.238... [Pg.1136]

Figure 6.29. Baeyer-Villiger reaction carried out continuously over 200 h under fluorous biphasic... Figure 6.29. Baeyer-Villiger reaction carried out continuously over 200 h under fluorous biphasic...
Cyclobutanone annulation onto a carbonyl group translates into y-butyrolactone annulation because of the facility of the Baeyer-Villiger reaction (Eq. 68 a)8). Indeed, the reaction proceeds sufficiently rapidly that even basic hydrogen peroxide effects the oxidation whereas, with less reactive carbonyl partners, peracids must be used. [Pg.50]

At this time, we can focus on the creation of the butenolide. Sulfur based methodoly allows simplification to the simple butanolide as in 170. While cyclobutanone spiroannulation of 171 followed by a Baeyer-Villiger reaction would create 170,... [Pg.74]


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1.2- Dicarbonyl compounds Baeyer-Villiger reaction

2-Thiaadamantane via Baeyer-Villiger reaction

Acyclic aliphatic Baeyer-Villiger reaction

Aldehydes Baeyer-Villiger reaction

Antirhine via Baeyer-Villiger reaction

Baeyer Villiger

Baeyer-Villiger Reaction arsten Bolm, Oliver Beckmann

Baeyer-Villiger oxidation Barton reaction

Baeyer-Villiger oxidation aldol reaction

Baeyer-Villiger oxidation reaction kinetics

Baeyer-Villiger reaction P-silicon atom

Baeyer-Villiger reaction biochemical

Baeyer-Villiger reaction buffers

Baeyer-Villiger reaction catalysts

Baeyer-Villiger reaction chemoselectivity

Baeyer-Villiger reaction competitive

Baeyer-Villiger reaction conformation

Baeyer-Villiger reaction electronic factors

Baeyer-Villiger reaction lactones

Baeyer-Villiger reaction mechanism

Baeyer-Villiger reaction peroxy acid

Baeyer-Villiger reaction radical scavengers

Baeyer-Villiger reaction regiochemistry

Baeyer-Villiger reaction regioselectivity

Baeyer-Villiger reaction side reactions

Baeyer-Villiger reaction stereochemistry

Baeyer-Villiger reaction substituent effects

Baeyer-Villiger reaction, asymmetric

C-Nucleosides via Baeyer-Villiger reaction

Catalytic Asymmetric Baeyer-Villiger Reactions

Cyclobutanones Baeyer-Villiger reaction

Cyclobutanones, asymmetric Baeyer-Villiger reaction

Cyclohexanone Baeyer-Villiger reaction

Ellipticine, 9-hydroxysynthesis via Baeyer-Villiger reaction

Erythronolide via Baeyer-Villiger reaction

Esters from Baeyer-Villiger reaction

Estrone via Baeyer-Villiger reaction

Functionalized ketones, oxidation Baeyer-Villiger reaction

Furan, 2,5-dimethoxy-2,5-dihydroSubject via Baeyer-Villiger reaction

Ginkgolide via Baeyer-Villiger reaction

Glycinoeclepin via Baeyer-Villiger reaction

Hydrazines synthesis using Baeyer- Villiger reaction

Hydrogen peroxide Baeyer-Villiger reaction

Hydrogenation-Baeyer-Villiger oxidation reaction

Hydroxy ketones Baeyer-Villiger reaction

In the Baeyer-Villiger reaction

Isoretronecanol via Baeyer-Villiger reaction

Isotopically substituted Baeyer-Villiger reaction

Ketones Baeyer-Villiger reaction

Ketones, alkyl phenyl Baeyer-Villiger reaction

Ketones, and Baeyer-Villiger reaction

Ketones, aryl alkyl Baeyer-Villiger reaction

Ketones, bridged bicyclic Baeyer-Villiger reaction

Ketones, bridged polycyclic Baeyer-Villiger reaction

Ketones, functionalized Baeyer-Villiger reaction

Ketones, fused ring bicyclic Baeyer-Villiger reaction

Ketones, fused ring polycyclic Baeyer-Villiger reaction

Ketones, monocyclic Baeyer-Villiger reaction

Ketones, unsaturated Baeyer-Villiger reaction

Lactones by Baeyer-Villiger reaction

Magnesium monoperoxyphthalate Baeyer-Villiger reaction

Microbial Baeyer-Villiger reactions

Mitomycin via Baeyer-Villiger reaction

Named reactions Baeyer-Villiger oxidation

Norbomenone Baeyer-Villiger reaction

Oxidation Baeyer-Villiger reaction

Oxidation of Ketones to Esters (Baeyer-Villiger Reaction)

Oxidations asymmetric Baeyer-Villiger reaction

Oxidative cleavage Baeyer-Villiger reaction

Pentaprismane via Baeyer-Villiger reaction

Peracetic acid Baeyer-Villiger reaction

Peracetic acid, trifluoroanti hydroxylation Baeyer-Villiger reaction

Peracids Baeyer Villiger reaction

Peroxycarboxylic acids Baeyer-Villiger reaction

Podocarpic acid, dimethoxysynthesis via Baeyer-Villiger reaction

Prostaglandins via Baeyer-Villiger reaction

Pseudocytidine via Baeyer-Villiger reaction

Ribofuranoside via Baeyer-Villiger reaction

Rifamycin via Baeyer-Villiger reaction

Stereospecific reactions Baeyer Villiger oxidation

Steroids Baeyer-Villiger reaction

Subject via Baeyer-Villiger reaction

The Baeyer-Villiger reaction

Thienamycin via Baeyer-Villiger reaction

Villiger

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