Transformations of peroxide olefin ozonolysis products under the action of hydroxylamine and semicarbazide hydrochlorides in isopropyl alcohol

Ishmuratov, G. Yu.; Legostaeva, Yu. V.; Garifullina, L. R.; Botsman, L. P.; Идрисова, З. И.; Муслухов, Р. Р.; Ишмуратова, Н. М.; Толстиков, Г. А.

doi:10.1134/s1070428013100011

Cited by 11 publications

(2 citation statements)

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“…, gave up to 65% of the corresponding isopropyl (R)-3-hydroxynonanoate (Scheme 6). 127 Finally the use of acetic acid instead of alcohols under similar reactions conditions leads to (R)-hydroxynonanoic acid in good yield (82%).…”

Section: Oxidative Cleavagementioning

confidence: 95%

Synthetic Transformations for the Valorization of Fatty Acid Derivatives

et al. 2017

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Oleochemistry is a growing field from the industrial point of view, and one of the basis for a more sustainable chemical production, less dependent of fossil sources. From this point of view, the development of selective and efficient synthetic transformations of triglycerides and fatty acids and esters is an active research field. This short review describes an overview of the most recent advances in the synthetic transformations of fatty acid derivatives into valuable chemicals. 1 Introduction 2 Triglycerides 2.1 Reactions on the ester group and multistep processes 2.2 Epoxidation 2.3 Ozonolysis 2.4 Cross metathesis 3 Reactions on the ester group of fatty acids and esters 3.1 Synthesis of free carboxylic acids 3.2 Synthesis of carboxylic esters 3.3 Reduction to alcohols and aldehydes 3.4 Synthesis of nitrogenated derivatives 4 Oxidation of Unsaturated Fatty acids and esters 4.1 Epoxidation and reactions of epoxides 4.2 Allylic oxidation 4.3 Synthesis of ketoderivatives 4.4 Oxidative cleavage 5 Addition reactions of unsaturated fatty acids and esters 5.1 Hydrogenation and hydroformilation 5.2 Cycloadditions and related reactions 5.3 Addition of carboxylic acids 5.4 Hydroalkylation 5.5 Radical additions 6 Other reactions of unsaturated fatty acids and esters 6.1 Cross metathesis 6.2 Isomerization 7 Conclusion and outlook

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Section: Oxidative Cleavagementioning

confidence: 95%

Synthetic Transformations for the Valorization of Fatty Acid Derivatives

et al. 2017

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“…First, unusual transformation of peroxy products under the action of semicarbazide hydrochloride in alcoholic solutions into the corresponding esters via formation of hemiacetals was discovered. Second, under the action of hydroxylamine hydrochloride, the initially formed aldehydes transformed into the individual products or their mixtures via the pathway aldoxime → nitrile → methyl or isopropyl ester, depending on the nature of the substrate and reaction conditions [12,13].…”

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confidence: 99%

One-pot ozonolytic synthesis of acyclic α,ω-bifunctional compounds from methyl 10-undecenoate and 10-undecen-1-ol

et al. 2015

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Transformations of peroxy products formed by ozonolysis of undecylenic acid derivatives (methyl ester and hydride reduction product, 10-undecen-1-ol) in various protic and aprotic solvents (МеОН, Pr i OH, tetrahydrofuran, 1 : 5 AcOH-CH 2 Cl 2 mixture), occurring under the action of such reductants as hydroxylamine and semicarbazide hydrochlorides, were studied. These reductants exhibit high performance and in some cases high chemoselectivity, which allowed the development of a number of one-pot procedures for the synthesis of acyclic α,ω-bifunctional compounds, the majority of which are widely used in medicine, perfumery, cosmetics, engineering, and chemical industry, e.g., as block synthons in targeted organic synthesis.

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