L. R. Garifullina

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

Hydroxylamine and semicarbazide hydrochlorides were shown to be efficient as reducing agents toward peroxide products of ozonolysis of various olefins with different degrees of substitution. The rate of the transformations aldehyde → aldehyde oxime → nitrile → ester upon treatment of peroxides with hydroxylamine hydrochloride in isopropyl alcohol was lower than in methanol.

Transformations of peroxide products of olefin ozonolysis under the action of semicarbazide in methanol

Peroxide products generated by ozonolysis of non-1-ene, 3-carene, stereoisomeric α-pinenes, (−)-limonene, and castor oil were subjected to transformations by the action of semicarbazide and hydrazine-1,2-dicarboxamide in methanol.

Ozonolysis of Unsaturated Compounds in the Synthesis of Insect Pheromones and Juvenoids

Research from the last 20 years on the use of ozonolysis of cyclic and acyclic mono- and dienes and aromatic compounds in various steps of the total synthesis of insect pheromones and juvenoids was reviewed.

OZONOLYTIC TRANSFORMATION OF (S)-(-)-LIMONENE IN HCl-ISOPROPANOL

Partial ozonolysis of (S)-(–)-limonene (ee 50%) in cyclohexane:isopropanol at 2–4°C formed the 1,2,4-trioxolane as a mixture of diastereomers in a 3:2 ratio. A solution of HCl in i-PrOH acted as a cleaving agent during decomposition of the peroxides and a cyclizing agent during formation of the diastereomeric 1,2,4-substituted cyclohexanes.

Transformation of peroxide products of olefin ozonolysis under treatment with hydroxylamine and semicarbazide hydrochlorides in acetic acid

Hydrochlorides of hydroxylamine and semicarbazide efficiently reduce peroxide products of olefin ozonolysis in a system CH2Cl2-AcOH leading to the formation of carboxylic acids and their derivatives. The application of water as the solvent component favors the increase in the fraction of nitrogen-containing organic compounds (semicarbazones, keto- and aldoximes, nitriles) and reduction in the yield of carboxylic acids.

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

Ozonolytic transformations of 10-undecenoic acid, which is available from castor oil, were studied. Syntheses of several α, ω-bifunctional sebacic acid derivatives were developed.

Transformations of peroxide olefin ozonolysis products in methanol in the presence of water

Transformations of peroxide products of ozonolysis of various olefins with different degrees of substitution at the double bond by the action of hydroxylamine and semicarbazide hydrochloride in methanol in the presence of water as co-solvent were studied.

Transformations by Tosylhydrazide of Peroxide Ozonolysis Products of ∆3-Carene, (–)-α-Pinene, and (S)-Limonene

Tosylhydrazide was shown to be an effective reductant in protic solvents for the peroxide ozonolysis products of ∆3-carene, (–)-α-pinene, and (S)-limonene. Either α,ω-ditosylhydrazones or α,ω-ketotosylhydrazonoacids were formed depending on the nature of the trisubstituted cycloalkene.

New method of preparation of alkoxyacetic acids

In this work, we report the results of lowtempera� ture ozonolysis of benzyl and phenyl allyl ethers for the preparation of methyl benzyland phenoxyace� tates. The esters of arylacetic acids were prepared by two methods: in the methanol-methylene chloride system in the presence of alkali at -65°C or in methanol at -78°C followed by the treatment of intermediate per� oxide products with semicarbazide hydrochloride. The ozonolysis of benzyl and phenyl allyl ethers Ia and Ib in the presence of NaOH was found to lead in high yield and selectivity to esters IIa and IIb, respectively. Byproducts formed in small amounts are the corre� sponding alkoxyacetic aldehydes IIIa and IIIb. At the same time, the treatment of primary ozonation prod� ucts (peroxides) with semicarbazide hydrochloride gives a mixture of esters IIa and IIb and acetals IVa and IVb (Table 1).

Transformations of Peroxide Products of Olefin Ozonolysis in Tetrahydrofuran in Reactions with Hydroxylamine and Semicarbazide Hydrochlorides

Treatment with hydroxylamine and semicarbazide hydrochlorides of peroxide products obtained by ozonolysis of olefins in tetrahydrofuran gives mainly carboxylic acids and their derivatives.