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A new mechanism for gas phase ozone–olefin reactions

✍ Scribed by H. Edward O'Neal; Carl Blumstein

Publisher
John Wiley and Sons
Year
1973
Tongue
English
Weight
829 KB
Volume
5
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

A new mechanism for gas phase ozone‐olefin reactions is proposed. The mechanism involves biradical intermediates which can react in a variety of ways. One of the possible reaction modes corresponds to the Criegie mechanism originally proposed to explain solution ozonolysis reactions and generally also accepted in the past for gas phase reactions. However, an examination of the gas phase data on ozone–olefin reactions and of the thermochemical and kinetic requirements for these reactions indicates that the Criegie reaction mode may be the least important of various other reaction possibilities. Those other reaction possibilities involve intramolecular H abstractions and rearrangements in biradical intermediates. The proposed mechanism provides very reasonable explanations for a number of unusual observations on gas phase ozonolysis. These are the formation of peroxidic bound products, aldehyde and 1,2‐dicarbonyl product fluorescences, and unexpected carbonyl product formations.

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