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

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, Pr i OH, tetrahydrofuran, 1: 5 AcOH–CH 2 Cl 2 mixture), occurring under the action of such reductants as...

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Bibliographic Details
Published in:Russian journal of applied chemistry 2015-06, Vol.88 (6), p.935-940
Main Authors: Legostaeva, Yu. V., Botsman, L. P., Nazarov, I. S., Yakovleva, M. P., Garifullina, L. R., Khalikov, R. M., Ishmuratov, G. Yu
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Industrial Chemistry/Chemical Engineering
Organic Synthesis and Industrial Organic Chemistry
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Summary: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, 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.
ISSN:1070-4272
1608-3296
DOI:10.1134/S1070427215060075