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

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 (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.