ChemInform Abstract: OZONIERUNG VON CYCLOHEXEN IN GEGENWART TERTIAERER AMINE

Transformations of peroxide products of olefins ozonolysis

“…Carbonyl compounds were obtained in one stage by the ozonolysis in the presence of pyridine [1] or tertiary aliphatic amines [49]. compounds can be isolated in good yield by a simple fi ltration.…”

Ozonolysis of Alkenes and Study of Reactions of Polyfunctional Compounds: LXVII. Synthesis of 27,27,27-Trifluoro-20-hydroxyecdysone Acetonides from 24,25- and 25,26-Anhydro-20-hydroxyecdysone Derivatives via Ozonolysis and Trifluoromethylation

“…By treatment with Me 3 SiCF 3 in the presence of Bu 4 N + F -(according to [9]) compounds I and III were converted into the corresponding 14-O-trimethylsilyl derivatives II and V. As followed from the intensity ratio of the signals from C 25 =C 24 H (δ 5.18 ppm, t, 3 J = 7.0 Hz) and C 25 =C 26 H 2 (δ 4.71 and 4.75 ppm, two singlets) in the 1 H NMR spectrum of II, the ratio of the ∆ 24,25 -and ∆ 25,26 -moieties is equal to ~2 : 1. Ozonolysis of silyl derivative II under different conditions (by the procedures reported in [7,8,10]) led to formation of a complex mixture of products. Unlike compound I, ozonolysis of 2,3-diacetoxy derivative VII according to [7] gave the expected mixture of ketone VIII and alcohol IX, which were separated by column chromatography.…”

“…Mixture III/IV was separated by column chromatography. The yield of ketone III obtained by the procedure described in [7] was greater than in the synthesis by ozonolysis [8] which was used by us previously [1] for the same purpose. By treatment with Me 3 SiCF 3 in the presence of Bu 4 N + F -(according to [9]) compounds I and III were converted into the corresponding 14-O-trimethylsilyl derivatives II and V. As followed from the intensity ratio of the signals from C 25 =C 24 H (δ 5.18 ppm, t, 3 J = 7.0 Hz) and C 25 =C 26 H 2 (δ 4.71 and 4.75 ppm, two singlets) in the 1 H NMR spectrum of II, the ratio of the ∆ 24,25 -and ∆ 25,26 -moieties is equal to ~2 : 1.…”

Transformations of peroxide ozonolysis products of natural olefins by N-containing organic compounds in methanol

“…In the middle of the twentieth century all these types of transformations of peroxide ozonolysis products were actively studied using a variety of reagents and thermal and photochemical degradation. However, in our opinion, N-containing organic compounds have seen limited use for these purposes and are represented in ozonolysis−reduction reactions by thiourea [1], tetracyanoethylene [2,3], pyridine [4], tertiary amines [5], and amino-N-oxides [6]; in ozonolysis−cleavage reactions by triethylamine in combination with water [3] or acetic anhydride [7][8][9].…”