Ozonolytic Transformations of 10-Undecenoic Acid in Various Solvents Through the Action of Hydroxylamine and Semicarbazide Hydrochlorides

Ishmuratov, G. Yu.; Legostaeva, Yu. V.; Nasibullina, G. V.; Garifullina, L. R.; Botsman, L. P.; Толстиков, Г. А.

doi:10.1007/s10600-014-1031-8

Cited by 3 publications

(3 citation statements)

References 5 publications

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“…R f 0.41 (petroleum ethermethyl tert-butyl ether, 2 : 1). The IR spectrum of the product is identical to that reported in [11]. The 1 Н and 13 С NMR spectra are identical to those reported in [35].…”

Section: Methodssupporting

confidence: 76%

“…R f 0.28 (petroleum ether-methyl tert-butyl ether, 2 : 1). The IR and 1 Н and 13 С NMR spectra are identical to those reported in [11].…”

Section: Methodssupporting

confidence: 67%

“…Ozonolytic transformations of unsaturated alcohol 2 were not studied. As shown previously [11], hydroxylamine and semicarbazide hydrochlorides are effective nitrogen-containing reductants of peroxy products of alkane ozonolysis, reducing them to the corresponding O-and N-functionalized derivatives in various protic and aprotic solvents (МеОН, Pr i OH, THF, AcOH-CH 2 Cl 2 ).…”

mentioning

confidence: 62%

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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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Section: Methodssupporting

confidence: 76%

“…R f 0.28 (petroleum ether-methyl tert-butyl ether, 2 : 1). The IR and 1 Н and 13 С NMR spectra are identical to those reported in [11].…”

Section: Methodssupporting

confidence: 67%

mentioning

confidence: 62%

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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 peroxide products of oleic acid ozonolysis at treatment with hydroxylamine and semicarbazide hydrochlorides

et al. 2015

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Peroxide products of oleic acid ozonolysis treated with semicarbazide and hydroxylamine hydrochlorides in methanol are predominantly converted into methyl nonanoate and dimethyl nonanedioate, in 2-propanol, into isopropyl nonanoate and monoisopropyl ester of nonanedioic acid, and also into nonanenitrile, in tetrahydrofuran and in a mixture of acetic acid with dichloromethane, into nonanoic and nonanedioc acids, and also in nonanal oxime and 9-(hydroxyimino)nonanoic acid.Oleic [(9Z)-octadec-9-enoic] acid 1 is present in the composition of nearly all natural fats and oils. One of its main sources is olive (~80%), and also sunflower (39%) and cottonseed (35%) oils, in animal fats it constitutes 36-45% of the overall amount of fatty acids [1].

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Hydroxylamine Reactions with Peroxide Products of Alkenes Ozonolysis

et al. 2018

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Ozonolytic Transformations of 10-Undecenoic Acid in Various Solvents Through the Action of Hydroxylamine and Semicarbazide Hydrochlorides

Cited by 3 publications

References 5 publications

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

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

Transformations of peroxide products of oleic acid ozonolysis at treatment with hydroxylamine and semicarbazide hydrochlorides

Hydroxylamine Reactions with Peroxide Products of Alkenes Ozonolysis

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