Ethylene ozonide

Dimethyl peroxide Diethyl peroxide Di-t-butyl-di-peroxyphthalate Difuroyl peroxide Dibenzoyl peroxide Dimeric ethylidene peroxide Dimeric acetone peroxide Dimeric cyclohexanone peroxide Diozonide of phorone Dimethyl ketone peroxide Ethyl hydroperoxide Ethylene ozonide Hydroxymethyl methyl peroxide Hydroxymethyl hydroperoxide... 

Ethylene Ozonide. C2H403 colorl, unpleasantsmelling oil mp, becomes lustrous at —80° bp,... 

Dimethyl peroxide Diethyl peroxide Di-t-butyl-di-peroxyphthalate Difuroyl peroxide Dibenzoyl peroxide Dimeric ethylidene peroxide Dimeric acetone peroxide Dimeric cyclohexanone peroxide Diozonide of phorone Dimethyl ketone peroxide Ethyl hydroperoxide Ethylene ozonide Hydroxymethyl methyl peroxide Hydroxymethyl hydroperoxide 1-Hydroxyethyl ethyl peroxide 1 -Hydroperoxy-1 -acetoxycyclodecan-6-one Isopropyl percarbonate Isopropyl hydroperoxide Methyl ethyl ketone peroxide Methyl hydroperoxide Methyl ethyl peroxide Monoperoxy succinic acid Nonanoyl peroxide (75% hydrocarbon solution) 1-Naphthoyl peroxide Oxalic acid ester of t-butyl hydroperoxide Ozonide of maleic anhydride Phenylhydrazone hydroperoxide Polymeric butadiene peroxide Polymeric isoprene peroxide Polymeric dimethylbutadiene peroxide Polymeric peroxides of methacrylic acid esters and styrene... 

Interaction may be explosive, owing to the very low stability of ethylene ozonide. See Combustible gases, above, also Ethylene ozonide... 

A detailed assignment of the IR absorption frequencies of 1,2,4-trioxolane (1) in solid argon was achieved by comparison with the spectra of various isotopically substituted species <82JPC3154>. Similarly, for a series of substituted 1,2,4-trioxolanes, characteristic IR bands obtained via matrix isolation were assigned and compared with those of 1,2,4-trioxolane (1) (ethylene ozonide) (Table 7) <82JPC4548>. The spectra of cis- and trani-1,2,4-trioxolanes indicate that the cis isomer has characteristic absorptions in the range 820-855 cm with the trans isomer at 1320-1360 cm . 

It has been suggested that there may be an important interaction between n orbitals on the three sulfur atoms with the CHj moieties which stabilizes the twist conformation in (2). It is possible that this is also an important factor in the stabilization of the twist hair of ethylene ozonide... 

Ozone reacts with organics, attacking most kinds of double bonds. It reacts with ethylene forming ethylene ozonide, a cyclic compound containing three oxygen atoms ... 

Molecular models, ethylene ozonides, 750 Molecular orbitals, dioxiranes, 27-9 Molecular oxygen... 

Figure 16. Analysis of the product spectra in Figure 14. (A) residual spectrum of Figure 14B (B) and (C) are reference spectra of ethylene ozonide and glycolaldehyde.

Ethylene ozonide is highly sensitive to shock. Pouring from one vessel into another has led to violent explosion (Ref 87)... 

The sole possibility of preparing the two parent compounds of the trioxolane series consists in the action of ozone on ethylene. When this ozonation was performed under suitable conditions, e.g. in a condensed phase at temperatures below -175 °C, the formation of 1,2,3-trioxolane (1) was observed (72JA4856, 81JA2578) (cf. Section 4.33.2.2.4). However, because of its thermal instability, this primary ozonide cannot be isolated but rearranged at temperatures above -100 °C to 1,2,4-trioxolane (2), ethylene ozonide, a colorless, explosive liquid extremely sensitive to impact (42LA(583)187>. The mechanism of the ring transformation (1) -> (2) has been discussed in Section 4.33.3.1.2. 

Here, pathway 1 (reaction 1) is the coordinated addition of ozone (1) to ethylene (2), which proceeds through the formation of a weakly-boimd complex that transforms into primary ethylene ozonide (PO) or 1.2.3-trioxolene upon passing through the symmetrical transient state (TSl). Pathway 2 (reaction 2, the DeMore mechanism [15]) involves the collision during spontaneous orientation of the reagents (3) and the rotational transition to the biradical transient state (TS2) (4) followed by the formation of the same PO. Proceeding from the above-said, we supplement this pathway with the reaction of detachment of molecular oxygen and the formation of intermediate biradical (5) the latter may either decompose with the formation of formaldehyde (6) and carbene (7) or transform into acetaldehyde (8) or epoxide (9). Finally, pathway 3 involves the transition of ozone into the triplet state (10). This pathway is similar to reaction 2. Here, the same biradical (5) is formed it transforms into the... 

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