Reactions of some stilbene ozonides with dimethyl sulphoxide and dimethylformamide

Abstract

Some stilbene ozonides react mith dimethyl THE recent report1 that ozonides are readily solvolysed by sulphoxide, dimethyfformamide, and primary, secondary alcohols prompts us to report our observations on the and tertiary amines to give a single aldehyde and a reactions of some stilbene ozonides with dimethyl sulphsingle acid in quantitative yield oxide, dimethylformamide, and amines The ozonides

Reactions of organic pollutants. 1. Ozonation of acenaphthylene and acenaphthene

“…The pathway proposed for the formation of 5 is given by Reaction Sequence 1: where the solvent-activated decomposition of the ozonide (3, 5) intermediate to the aldehydic acid is followed by ring-chain (A-3) Figure 2. Liquid-liquid extraction of products from ozonation of acenaphthylene (1) in water tautomerism (4) to form a lactone-hemiacetal intermediate (10), which subsequently forms the lactone-methoxyacetal (5) by reaction with the methanol solvent.…”

“…The methoxyacetal (5) and the dimethyl ester of the diacid, 9, were identified in fraction A-3. These observations confirm that both the diacid 9 and the hemiacetal 10 were products of the ozonation in water.…”

Transformations of peroxide products of olefins ozonolysis

“…In water environment the ozonides are cleaved reluctantly. However in the presence of strong solvating solvents (DMSO, DMF, amines) the fragmentation of stilbene ozonide 18 occurred quickly and quantitatively [3] yielding benzaldehyde 19 and benzoic acid 20. The solvolysis of ozonides proceeds with the same rate in the neutral and weakly acidic environment; it accelerates in alkaline solution.…”

“…Castaneum (4R,8S)-enantiomer, and also 4R-methylnonan-1-ol 195 [102]. The decisive stage of the synthesis of pheromones 194 and 195 is the ozone cleavage of the intermediate (6R)-6,10-dimethyl-9-undecen-2-one 192 by the use of NaBH(OAc) 3 as the reducer that allowed the preparation of exclusively (6R)-6-methyl-9-hydroxynonan-2-one 193 in a high yield and good chemoselectivity (Scheme 41).…”

Thermal Decomposition of Phospholipid Secondary Ozonides: Implications for the Toxicity of Inhaled Ozone

“…Secondary ozonides thermally decompose (see, e.g., Criegee et al, 1953Criegee et al, , 1955Bailey, 1956;Bailey & Mainthia, 1956;Bernatek & Hvatum, 1960;Greiner & Mueller, 1962;Pasero et al, 1963;Briner et al, 1965;Privett & Nickell, 1966;Razumovskii & Yur'ev, 1967;Story et al, 1968aStory et al, , 1968bEllam & Padbury, 1971;Criegee & Korber, 1972;Hull et al, 1972;Ewing et al, 1989aEwing et al, , 1989bAnachkov et al, 1994). Free radicals are generated in the decomposition of simple ozonides such as allylbenzene ozonide, as indicated by the values of the Arrhenius parameters for their thermal decomposition, by the nature of the products in various solvents, and by the use of spin traps (Ewing et al, 1989b).…”