Oxidation of secondary alcohols with ozone

Waters, William L.; Rollin, Anthony J.; Bardwell, Cindy M.; Schneider, Jeffrey A.; Aanerud, Thomas W.

doi:10.1021/jo00867a033

Cited by 27 publications

(11 citation statements)

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“…A number of authors have tried to elucidate the kinetics and mechanism of the ozonolysis of alcohols and their application to the selective preparation of ketones and aldehydes in high yields under mild conditions [3,[39][40][41][42][43][44][45][46]. The basic concepts of such reactions are discussed in several references [1,2,25,34,35,39].…”

Section: Alcoholsmentioning

confidence: 99%

“…The widest application, in this respect, has been found for the oxidation of primary and secondary alcohols respectively into their corresponding aldehydes and ketones. For example in the cases of the oxidation of open-chain (simple) and cyclic secondary alcohols the yield of ketones is within the range of 57-83 % [3]. Moreover, the considered interactions are extremely important from an ecological point of view for the utilization and purification of industrial wastewaters, originating from hydroxybenzene production, through their partial or complete oxidation .…”

Section: Introductionmentioning

confidence: 99%

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Kinetics and Mechanism of the Ozone Reaction with Alcohols, Ketones, Ethers and Hydroxybenzenes

Rakovsky¹,

Anachkov²,

Belitskii³

et al. 2016

ChChT

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Abstract. The review, based on 92 references, is focused on degradation of organics by ozonation and it comprises various classes of oxygen-containing organic compounds -alcohols, ketones, ethers and hydroxybenzenes. The mechanisms of a multitude of ozone reactions with these compounds in organic solvents are discussed in details, presenting the respective reaction schemes. The corresponding kinetic parameters are given and some thermodynamic parameters are also listed. The dependences of the kinetics and the mechanism of the ozonation reactions on the structure of the compounds, on the medium and on the reaction conditions are revealed. Various possible applications of ozonolysis are specified and discussed. All these reactions have practical importance for the protection of the environment.

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Section: Alcoholsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Kinetics and Mechanism of the Ozone Reaction with Alcohols, Ketones, Ethers and Hydroxybenzenes

Rakovsky¹,

Anachkov²,

Belitskii³

et al. 2016

ChChT

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“…Other suitable oxidants are ozone [31], potassium permanganate [32], silver peroxy disulfate [33], nitrogen dioxide [34], and tert-butyl hypochlorite -pyridine [35].…”

Section: Chemical Propertiesmentioning

confidence: 99%

Pentanols

Lappe

Hofmann

2011

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Physical Properties 3. Chemical Properties 4. Production 5. Uses 6. Quality Specifications and Chemical Analysis 7. Storage and Transportation 8. Toxicology and Occupational Health

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“…The oxidation of secondary alicyclic alcohols with ozone is known (24). Therefore, in view of the proposed intermediacy of allylic alcohol in ozonations under study, it was of interest to investigate the reaction of a model steroidal allylic alcohol with ozone in ethyl acetate at -78OC.…”

Section: Printed In Canadamentioning

confidence: 99%

Tetracyclic triterpenes. X. Solvent effect in reactions of tetrasubstituted triterpenoidal olefins with ozone. An allylic oxidation

Paryzek¹,

Martynow²

1988

Can. J. Chem.

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ZDZISLAW PARYZEK and JACEK MARTYNOW. Can. J. Chem. 66, 2130 (1988). The highly hindered 8,9 double bond in lanostane derivatives was found susceptible to oxidation with ozone. The reaction depends on the polarity of the solvent. It is proposed that the structure of the initial complex formed between the olefin and ozone is influenced by the reaction medium. Reaction of 3P-acetoxy-5a-lanost-8-ene with ozone gives 8a,9a-epoxide in methylene chloride, while 3P-acetoxy-5a-lanost-8-en-7-one, an allylic oxidation product, is the main compound formed in ethyl acetate.ZDZISLAW PARYZEK et JACEK MARTYNOW. Can. J. Chem. 66, 2130Chem. 66, (1988. On a trouvC que la double liaison trks empEchke que l'on retrouve dans les positions 8,9 des dCrivCs du lanostane est trks susceptible aux oxydations par l'ozone. La rkaction est influencCe par la polarit6 du solvant. On suggkre que la structure du complexe qui se forme initialement entre 1'olCfine et l'ozone est influencCe par le milieu rkactionnel. Dans le chlorure de mtthylkne, la rkaction de 1'acCtoxy-3P 5a-lanosthe-8 avec l'ozone conduit a l'tpoxyde 8a,9a; par ailleurs, dans 1'acCtate d'tthyle, le produit principal est I'acCtoxy-3P 5a-lanosthe-8 one-7, un produit provenant d'une oxydation allylique.[Traduit par la revue]Retropinacolic rearrangement of a triterpene 3-alcohol, for example 5a-lanostan-3P-01 (I), under the action of phosphorus pentachloride leads to the ring A contracted isopropylidene compound (11). Treatment of the olefin (11) with ozone provides a simple method of preparation of A-nor steroids (111). The sequence shown in eq.[ l ] has been described for pentacyclic (1) 111 and tetracyclic (2) triterpenes, their derivatives possessing a degraded side chain (3), and for 4,4-dimethyl steroids (4). In the lanostane series, 14a-methyl-A-nor-steroids were prepared by this simple degradation route (5).The literature search revealed, however, that ozonolysis of 3-izopropylidene-A-nor-steroids was only rarely performed on substrates possessing an additional olefinic double bond in the molecule. In these cases the reported yields of the degraded compounds were low (15-45%) ( l a , 6).In our approach to 14a-methyl-A-nor-5a-cholest-8-en-3-one (9), the isopropylidene compound 4, which was prepared from 'For Part IX, see ref. 9. 2Author to whom correspondence may be addressed. 3~evision received March 28, 1988. dihydrolanosterol (I), was subjected to oxidative degradation with ozone. The reaction carried out in methylene chloride at -78°C gave the keto-diene 5, which isomerized during work-up to the 5P-isomer 6 (26). Thin-layer chromatographic monitoring of the reaction showed that the epoxy-ketone 7 was the primary product of the reaction. Dehydration of 7 to the diene 5 was catalyzed by an acid4 formed from the solvent under ozonolysis conditions (7). This was evidenced by the isolation of the epoxy-ketone 7 (5 1 % yield) and the enone 9 (5%) from the reaction of 4 carried out in the same solvent containing a small amount of pyridine (8). In the course of the ozonolysi...

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Oxidation of secondary alcohols with ozone

Cited by 27 publications

References 0 publications

Kinetics and Mechanism of the Ozone Reaction with Alcohols, Ketones, Ethers and Hydroxybenzenes

Kinetics and Mechanism of the Ozone Reaction with Alcohols, Ketones, Ethers and Hydroxybenzenes

Pentanols

Tetracyclic triterpenes. X. Solvent effect in reactions of tetrasubstituted triterpenoidal olefins with ozone. An allylic oxidation

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