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University of Illinois at Urbana-Champaign
Lithiation of Alkyl 2,6-Substituted Benzoates Adjacent to Oxygen: Alpha-Lithioalkyl Alcohol Synthons
Abstract
dc:descriptionThe removal of an sp('3) proton alpha to the bivalent oxygen of an ether or alcohol to generate a formal stable (alpha)-oxocarbanion is unknown. However, formation of an (alpha)-lithio alcohol derivative from an ester might be feasible because the formally bivalent oxygen has a partial positive charge which could provide dipole-stabilization of the formal adjacent carbanion. In order to achieve the formation of an (alpha)-oxocarbanion from an ester by direct proton removal, it would be necessary to select structures in which proton removal and nucleophilic addition to the ester carbonyl are not competitive with metalation.
Degree
thesis:*- 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 and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Carter, Linda Gay
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (UMI)AAI8108460
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/67236