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

doi:10.1134/S1070427215060075

Paper

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

Published Sep 30, 2015 · Yu. V. Legostaeva, L. P. Botsman, I. S. Nazarov

Russian Journal of Applied Chemistry

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Abstract

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 (MeOH, PriOH, tetrahydrofuran, 1: 5 AcOH–CH2Cl2 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.

Study Snapshot

One-pot ozonolytic synthesis of acyclic,-bifunctional compounds from methyl 10-undecenoate and 10-undecen-1-ol allows for the production of compounds used in medicine, perfumery, cosmetics, engineering, and chemical industry.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

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

References

Gas sensing and photoluminescence of flower-like ZnO hollow microspheres synthesised using facile solvothermal method

Flower-like ZnO microspheres synthesised using solvothermal method show potential for gas sensing and photoluminescence applications, with a linear relationship between gas content and sensitivity.

Sustainable route to methyl-9-hydroxononanoate (polymer precursor) by oxidative cleavage of fatty acid methyl ester from rapeseed oil

This sustainable method converts rapeseed oil's fatty acid methyl esters into polymer precursors, with 85% methyl-9-hydroxynonanoate, under mild conditions and with valuable by-products.

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

Hydroxylamine and semicarbazide hydrochlorides effectively reduce peroxide products from ozonolysis of various olefins, with a slower rate of transformation in isopropyl alcohol compared to methanol.

Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII. Investigation of transformations of peroxide products of olefins ozonolysis treated with hydroxylamine hydrochloride

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Simple Preparation of Highly Pure Monomeric ω-Hydroxycarboxylic Acids

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Stille reactions catalytic in tin: a "Sn-F" route for intermolecular and intramolecular couplings.

This study demonstrates a catalytic "Sn-F" route for intermolecular and intramolecular couplings in tin, minimizing hazards and purification problems associated with organotin waste removal.

Citations

Hydroxylamine Reactions with Peroxide Products of Alkenes Ozonolysis

Hydroxylamine can directly transform alkenes into keto- and aldoximes without the need for preparation and isolation of carbonyl compounds.