The ozonolysis of trifluoroethylene, 1, 1-difluoroethylene, and perfluoroethylene. Epoxide and ozonide formation

JW Agopovich, CW Gillies

Index: Agopovich, John W.; Gillies, Charles W. Journal of the American Chemical Society, 1980 , vol. 102, # 25 p. 7572 - 7574

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Citation Number: 14

Abstract

It is likely that the initial attack of ozone on the olefin is governed by the electron-withdrawing effects of the fluorine atoms. Huisgen has mentioned that the electrophilic attack of ozone as in I can be treated as a 1, 3-dipolar cycloaddition." Hence, he reasoned that chlorinated and fluorinated alkenes are poor 1, 3-dipolarophiles due to a decrease in electron density of the double bond. The present results are consistent with this trend. Perfluoroethylene will not ...