The Endocyclic Restriction Test: Mechanistic Investigations of Sulfur and Oxygen Transfer Reactions
Jarboe, Stephen Gary
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https://hdl.handle.net/2142/84079
Description
Title
The Endocyclic Restriction Test: Mechanistic Investigations of Sulfur and Oxygen Transfer Reactions
Author(s)
Jarboe, Stephen Gary
Issue Date
2002
Doctoral Committee Chair(s)
Beak, Peter
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
Language
eng
Abstract
Mechanistic elucidation of an oxygen transfer reaction was sought by the application of the endocyclic restriction test toward an aldehyde-mediated epoxidation of olefins by molecular oxygen. The differentiation between alternate oxygen transfer reagents is provided by stereochemical studies, and well as by results from the endocyclic restriction test. Support for a radical chain mechanism that relies on an acylperoxy radical as the active oxidant is provided. Subsequent decarboxylation and epoxide ring-opening are proposed to rationalize the furan product obtained from the reaction.
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