Décomposition du percarbonate de O,O-t-butyle et O-isopropényle en solution dans des cyclanes |
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Authors: | R Jaouhari C Filliatre B Maillard JJ Villenave |
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Institution: | Laboratoire de Chimie Appliquée, Université de Bordeaux I, 351, cours de la Libération, 33405 Talence-Cédex, France |
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Abstract: | Thermolysis of O,O-t-butyl and O-isopropenyl percarbonate in cyclohexane involves free-radical acetonylation of solvent. Free radicals derived from solvent add to the percarbonate double bond and after a double β-scission reaction, cyclohexylacetone carbon dioxide and t-butoxy radicals are formed. Abstracting H atoms from the solvent, t-butoxy radicals regenerate free radicals from solvent, and the reaction becomes a chain process. Extending the study to other cycloalkanes it has been shown that the process is a general synthesis method for cycloalkylacetones. On the other hand, competitive reactions of pairs of solvents have shown that the reactivity of the substrates depends on H atom lability and on more complex phenomena like transfers between hydrocarbons and C-centered free-radicals. |
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