Preparation and Chemiluminescence of Cyclopropyl-Substituted Malonyl Peroxides
Darmon, Michael John
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https://hdl.handle.net/2142/70187
Description
Title
Preparation and Chemiluminescence of Cyclopropyl-Substituted Malonyl Peroxides
Author(s)
Darmon, Michael John
Issue Date
1982
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Abstract
4-Spiro{(2'-spirocyclopropyl)-cyclohexyl}-1,2-dioxolane-3,5-dione (2) and 4-cyclopropyl-4-methyl-1,2-dioxolane-3,5-dione (1) are prepared by the reaction of dicyclohexylcarbodiimide and hydrogen peroxide with the parent malonic acids. Chemiluminescence is observed when the cyclopropyl-substituted malonyl peroxides, 1 and 2, are heated in the presence of added aromatic fluorescers. The chemiluminescence is explained by the activated CIEEL mechanism with the aromatic fluorescer and malonyl peroxide. A cyclopropylcarbinyl-allylcarbinyl radical rearrangement is proposed to be involved in the chemiluminescence mechanism.
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