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

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

“…Me(H 2 C) 7 (CH 2 ) 7 Compounds 2, 3 and 6 at the use of hydroxylamine hydrochloride form evidently along the previously suggested route [16]: aldehyde 17 → aldoximes 4, 6 → nitriles 12, 14 → acids 2, 3 (Scheme 4).…”

“…R f 0.59 (petroleum ethertert-butyl methyl ether, 2 : 1). IR, 1 Н and 13 С NMR spectra are identic to those previously described [16,17].…”

Transformations of peroxide products of olefins ozonolysis

“…These cycloolefi ns were in high yield and with high selectivity converted into ketoester 134 and diketone 136 [60]. However at the use of this reagent in the ozonolysis of cycloolefi ns with more complex structure, Δ 3 -carene 137 and (+)-α-pinene 139, both at room temperature and at boiling hydroxyiminoesters 138 and 140 were obtained [61].…”

“…Recently the ozonolysis of cyclooctene 16 (n = 6) with equimolar amount of ozone at 0°C in methanol with subsequent treatment with hydroxylamine hydrochloride resulted in a mixture of dimethyl octanedioate 53 and nitriloester 129, 1:1 [60] (Scheme 21).…”

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

“…First, unusual transformation of peroxy products under the action of semicarbazide hydrochloride in alcoholic solutions into the corresponding esters via formation of hemiacetals was discovered. Second, under the action of hydroxylamine hydrochloride, the initially formed aldehydes transformed into the individual products or their mixtures via the pathway aldoxime → nitrile → methyl or isopropyl ester, depending on the nature of the substrate and reaction conditions [12,13].…”