Synthesis and Chemiluminescent Investigation of Malonyl Peroxides

The three malonyl peroxides 4-methyl-4-phenyl-1,2-dioxolane-3,5-dione (3), 4-diphenylmethyl-4-methyl-1,2-dioxolane-3,5-dione (4), and 4-methyl-4-(1-propenyl)-1,2-dioxolane-3,5-dione (5) are prepared by the methanesulfonic acid catalyzed reaction of hydrogen peroxide with the parent malonic acids. Weak chemiluminescence is observed from all three peroxides when they are thermolyzed in the presence of an aromatic fluorescer. The CIEEL mechanism is applied to explain the production of the light in each system. The production of the light in each case is very inefficient. The attempted synthesis of a fourth malonyl peroxide, 4-methyl-4-(trans-(beta)-styryl)-1,2-dioxolane-3,5-dione (6), is also presented.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Porter, Judith Elizabeth

• Chemistry, Organic

Identifier

(UMI)AAI8521861

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70303