Relative Rates of Reaction of Ozone With Olefins in the Vapor Phase

Relative rates of reaction of ozone with a number of olefins in the vapor phase have been determined by the use of the competitive method and GLC analysis of the reaction products. The results indicate a basic electrophilic trend onto which is superimposed a trend due to a partially inhibiting effect of the substituent groups, in particular of those on the more substituted carbon atom of the olefinic double bond. The results are discussed particularly in terms of a two-step addition process, involving an initial formation of an ozone–olefin π-complex and a slower rearrangement of the π-complex into the cyclic "initial ozonide".