Ozonolysis. X. Molozonide as an intermediate in the ozonolysis of cis- and trans-alkenes

Durham, Lois J.; Greenwood, Fred L.

doi:10.1021/jo01268a068

Cited by 32 publications

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“…A three‐step sequence outlined below Scheme was proposed by Criegee during the 1950s 1. This mechanism has been favored by many experimental studies 2–4. Gillies et al calculated the first‐step of the Criegee mechanism on the ethylene with the ozone reaction 5–11 and thought that the product of the first‐step ( MP ) was a concerted 1,3‐dipolar cyclo‐addition between ozone and ethylene.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of reaction mechanism for CH₂CHX(XH, F, Cl) with ozone

Deng

et al. 2004

Int J of Quantum Chemistry

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ABSTRACT:In this work, we study the reaction mechanism of the CH 2 CHX(XAH, F, Cl) with ozone reactions, using ab initio MP2 method at 6-311ϩϩg** basis set level. The geometric configurations of reactants, intermediates, transition states, and products were optimized, and the energies were obtained at the QCISD(T)/6-311ϩϩG** level. The transition states and intermediates of the reactions were verified by the vibrational analysis. The results show that the ozonolysis of ethylene and its derivatives is reasonable and believable along the Criegee mechanism. The results also show that the activation energies of the controlling steps along the fluoroethylene and chloroethylene with ozone reaction pathways were lower than that along the ethylene with ozone reaction pathway. That is to say, the derivatives of ethylene have the higher activity to react with ozone and deplete the ozone layer.

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Section: Introductionmentioning

confidence: 99%

Theoretical study of reaction mechanism for CH₂CHX(XH, F, Cl) with ozone

Deng

et al. 2004

Int J of Quantum Chemistry

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“…According to molecular weight (268, cryoscopically in benzene) and spectroscopic data, compound (6) (1,4-dichloro-1,4-epoxy-l H,4H-naphtho[ 1, 8-de][1,2]dioxepin) is a monomeric ozonide. The EI mass spectrum shows the molecular ion with characteristic isotope distribution for two C1 atoms at m/e=268.…”

Section: Ozonolysis Of 12-dichloroacenaphthylenementioning

confidence: 99%

“…For further differentiation between primary ozonide and normal ozonide, either the larger thermal stability of (6), or the difference in behavior of (5) and (6) towards tetracyanoethylene (TCNE) can be cons~lted['~. While (5) is no longer detectable after a short while in the presence of TCNE, (6) remains unchangedl'l. The reaction sequence (5) + (6) (TLC detection) under the conditions of ozonolysis is important for the assignment.…”

Section: Ozonolysis Of 12-dichloroacenaphthylenementioning

confidence: 99%

Ozonolysis of 1,2‐Dichloroacenaphthylene

Seltzer

Gäb

Körte

1980

Angew. Chem. Int. Ed. Engl.

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yellowish fluorescence were obtained after treatment of the natural material with M n 0 2 in acetic acid solution; they were regarded as possible unconjugated pteridines. However, since none of these products could be identified by chromatographic or spectroscopic methods as one of the natural pterins we have re-investigated them. First of all, the component showing the greatest migration on chromatography on cellulose with n-propanol/l% ammonia (2/1) (R,= 0.48) was

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“…Die Struktur des Prim‰rozonids als 1,2,3-Trioxolan wurde 1966 von Bailey et al [5] 1 H-NMRspektroskopisch nachgewiesen. Eine weitere Best‰tigung lieferten 1968 Durham und Greenwood [6] f¸r verwandte (Z)-und (E)-Olefine in CCl 2 F 2 bei À 1308. Trotzdem traten in den vorgenannten Arbeiten viele unerkl‰rliche Resultate auf, weshalb 1978 Ramachandran und Murray [7] die Ozonolyse von 1 nochmals im Detail untersuchten.…”

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Der Mechanismus der Alken‐Ozonolyse – eine kritische Betrachtung

Schank

2004

Helvetica Chimica Acta

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The Mechanism of Alkene Ozonolysis ± a Critical Examination Alkene ozonolyses have been carried out in experimental organic chemistry for more than a century, and a lucid description of the underlying reaction mechanism has been developped and integrated in most chemistry textbooks. Nevertheless, there are a great number of exceptions hard to rationalize by the accepted mechanism. Attempts in the past to give more-convincing answers to this problem failed. Therefore, the search for an alternative mechanistic model without contradictions is compelling. The present paper offers a redox model based upon the known properties of ozone both as a strong oxidant and an O-atom-transferring agent, especially when reacted with alkenes of sufficiently high electron density to act as reducing partners. Harries

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Ozonolysis. X. Molozonide as an intermediate in the ozonolysis of cis- and trans-alkenes

Cited by 32 publications

References 0 publications

Theoretical study of reaction mechanism for CH₂CHX(XH, F, Cl) with ozone

Theoretical study of reaction mechanism for CH₂CHX(XH, F, Cl) with ozone

Ozonolysis of 1,2‐Dichloroacenaphthylene

Der Mechanismus der Alken‐Ozonolyse – eine kritische Betrachtung

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Ozonolysis. X. Molozonide as an intermediate in the ozonolysis of cis- and trans-alkenes

Cited by 32 publications

References 0 publications

Theoretical study of reaction mechanism for CH2CHX(XH, F, Cl) with ozone

Theoretical study of reaction mechanism for CH2CHX(XH, F, Cl) with ozone

Ozonolysis of 1,2‐Dichloroacenaphthylene

Der Mechanismus der Alken‐Ozonolyse – eine kritische Betrachtung

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Theoretical study of reaction mechanism for CH₂CHX(XH, F, Cl) with ozone

Theoretical study of reaction mechanism for CH₂CHX(XH, F, Cl) with ozone